【结 构 式】 |
【分子编号】59251 【品名】methyl 3-chloro-4-cyclohexylbenzoate 【CA登记号】 |
【 分 子 式 】C14H17ClO2 【 分 子 量 】252.74048 【元素组成】C 66.53% H 6.78% Cl 14.03% O 12.66% |
合成路线1
该中间体在本合成路线中的序号:(XII)A different synthetic strategy was further reported. Fischer esterification of 4-cyclohexylbenzoic acid (VIII) with MeOH and H2SO4, followed by aromatic nitration of the resultant benzoate ester (IX), yielded methyl 4-cyclohexyl-3-nitrobenzoate (X). Nitro group reduction in (X) by transfer hydrogenation provided amine (XI). This was converted to the chloro derivative (XII) by application of a modified Sandmeyer reaction with tert-butyl nitrite and cupric chloride. Ester group reduction in (XII) with LiBH4, followed by Swern oxidation of the resultant alcohol (XIII), furnished aldehyde (XIV). The aminoethyl phosphonium salt (XVI) was prepared by addition of N-ethyl cyclohexylamine (VI) to vinyl triphenylphosphonium bromide (XV). The corresponding ylide generated in situ from phosphonium salt (XV) and potassium bis(trimethylsilyl)amide was then subjected to a Wittig reaction with aldehyde (XIV) to afford the title (Z)-propenyl amine.
【1】 Burgess, L.E.; The preparation of immunosuppressant SR-31747. Synth Commun 1997, 27, 12, 2181. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 59245 | N-Ethylcyclohexanamine; N-Ethylcyclohexylamine; Vulkacit HX | 5459-93-8 | C8H17N | 详情 | 详情 |
(VIII) | 59247 | 4-Cyclohexylbenzoic acid | 20029-52-1 | C13H16O2 | 详情 | 详情 |
(IX) | 59248 | 4-Cyclohexylbenzoic acid methyl ester; Methyl 4-cyclohexylbenzoate | 92863-34-8 | C14H18O2 | 详情 | 详情 |
(X) | 59249 | methyl 4-cyclohexyl-3-nitrobenzoate | C14H17NO4 | 详情 | 详情 | |
(XI) | 59250 | methyl 3-amino-4-cyclohexylbenzoate | C14H19NO2 | 详情 | 详情 | |
(XII) | 59251 | methyl 3-chloro-4-cyclohexylbenzoate | C14H17ClO2 | 详情 | 详情 | |
(XIII) | 59252 | (3-chloro-4-cyclohexylphenyl)methanol | C13H17ClO | 详情 | 详情 | |
(XIV) | 59253 | 3-chloro-4-cyclohexylbenzaldehyde | C13H15ClO | 详情 | 详情 | |
(XV) | 59254 | triphenyl(vinyl)phosphonium bromide | C20H18BrP | 详情 | 详情 | |
(XVI) | 59255 | {2-[cyclohexyl(ethyl)amino]ethyl}(triphenyl)phosphonium bromide | C28H35BrNP | 详情 | 详情 |