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【结 构 式】 
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【分子编号】56374 【品名】Methyl hydrogen octane-1,8-dioate; Monomethyl suberate; Octanedioic acid monomethyl ester; Suberic acid monomethyl ester 【CA登记号】3946-32-5 |
【 分 子 式 】C9H16O4 【 分 子 量 】188.22364 【元素组成】C 57.43% H 8.57% O 34% |
合成路线1
该中间体在本合成路线中的序号：(I)Monomethyl suberate (I) is treated with isobutyl chloroformate to produce the mixed anhydride (II), which is subsequently coupled with 3-aminopyridine (III), yielding amide (IV). The methyl ester group of (IV) is finally converted to the target hydroxamate upon treatment with methanolic hydroxylamine.
| 【1】 Gilbert, J.; et al.; A phase I dose escalation and bioavailability study of oral sodium phenylbutyrate in patients with refractory solid tumor malignancies. Clin Cancer Res 2001, 7, 8, 2292. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 56374 | Methyl hydrogen octane-1,8-dioate; Monomethyl suberate; Octanedioic acid monomethyl ester; Suberic acid monomethyl ester | 3946-32-5 | C9H16O4 | 详情 | 详情 |
| (II) | 56375 | C14H24O6 | 详情 | 详情 | ||
| (III) | 33327 | 3-Pyridinylamine; 3-Aminopyridine; 3-Pyridinamine | 462-08-8 | C5H6N2 | 详情 | 详情 |
| (IV) | 56376 | methyl 8-oxo-8-(3-pyridinylamino)octanoate | C14H20N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)3-(Benzyloxy)aniline (I) is acylated by suberic acid mono-methyl ester (II) either employing EDC as the coupling reagent or via activation with oxalyl chloride to produce the suberoyl anilide (III). Further displacement of the methyl ester group of (III) with hydroxylamine in the presence of NaOMe leads to the target hydroxamic acid
| 【1】 Belvedere, S.; Zhou, W.; Witter, D.; Yan, J.; Chen, W.; Secrist, J.P.; Richon, V.; Miller, T.; SAHA derived inhibitors of histone deacetylase (HDAC). 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 102. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 63471 | 3-[(phenylmethyl)oxy]aniline; 3-[(phenylmethyl)oxy]phenylamine | C13H13NO | 详情 | 详情 | |
| (II) | 56374 | Methyl hydrogen octane-1,8-dioate; Monomethyl suberate; Octanedioic acid monomethyl ester; Suberic acid monomethyl ester | 3946-32-5 | C9H16O4 | 详情 | 详情 |
| (III) | 63472 | methyl 8-oxo-8-({3-[(phenylmethyl)oxy]phenyl}amino)octanoate | C22H27NO4 | 详情 | 详情 |