(R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate | 187404-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate
• 英文别名: [(1R,2E)-2-benzylidenecyclohexyl] acetate
• CAS: 187404-46-2
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: YFKAECUOWLCMMW-ATGUSINASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate 在 sodium periodate 、 rhodium(III) chloride hydrate 、 copper(l) chloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.25h， 生成 (R)-(-)-2-(4-methylpentyl)cyclohexan-1-one
  参考文献：
  名称：

  金属和酶催化从环烯丙基醇制得酮和内酯的对映选择性路线

  摘要：

  已经开发了合成对映体纯的α-取代的酮和相应的内酯的通用且有效的途径。钌和酶催化的动态动力学拆分（DKR）以及随后的Cu催化的α-烯丙基取代是该路线的关键步骤。以高收率和优异的对映体过量获得α-取代的酮。通过随后的Baeyer-Villiger氧化，该方法学被用于合成天然己内酯（R）-10-甲基-6-十一烷醇。

  DOI：

  10.1021/ol302358j
• 作为产物：
  描述：

  苯甲醛 在 sodium tetrahydroborate 、 candida antarcticalipase B 、 C₁₂H₁₆ClO₂Ru 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 122.25h， 生成 (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate
  参考文献：
  名称：

  金属和酶催化从环烯丙基醇制得酮和内酯的对映选择性路线

  摘要：

  已经开发了合成对映体纯的α-取代的酮和相应的内酯的通用且有效的途径。钌和酶催化的动态动力学拆分（DKR）以及随后的Cu催化的α-烯丙基取代是该路线的关键步骤。以高收率和优异的对映体过量获得α-取代的酮。通过随后的Baeyer-Villiger氧化，该方法学被用于合成天然己内酯（R）-10-甲基-6-十一烷醇。

  DOI：

  10.1021/ol302358j

文献信息

• Chemoenzymatic Dynamic Kinetic Resolution of Allylic Alcohols:  A Highly Enantioselective Route to Acyloin Acetates
  作者：Krisztián Bogár、Pilar Hoyos Vidal、Andrés R. Alcántara León、Jan-E. Bäckvall

  DOI：10.1021/ol071395v

  日期：2007.8.1

  Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to give the corresponding acylated acyloins in high yields without loss of chiral information.

  用南极假丝酵母脂肪酶B（CALB）和钌催化剂1进行了一系列位阻烯丙基醇的动态动力学拆分（DKR）。将得到的光学纯净的烯丙基乙酸酯进行氧化裂解，以高产率得到相应的酰化酰化酰胆碱。不会丢失手性信息。
• One-pot synthesis and resolution of chiral allylic alcohols
  作者：Ahmed Kamal、Mahendra Sandbhor、Ahmad Ali Shaik、V. Sravanthi

  DOI：10.1016/s0957-4166(03)00598-6

  日期：2003.9

  Substituted alpha,beta-unsaturated ketones were selectively reduced to the corresponding allylic alcohols under mild reaction conditions. The allylic alcohols thus obtained were kinetically resolved by lipase catalyzed transesterification in the same pot to afford chiral allylic alcohols in excellent enantioselectivity. Various lipases were screened for this one-pot transesterification of allylic alcohols. Effects of different solvent have also been studied under these conditions. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) and on diatomaceous earth (PS-D) catalyzes this transesterification in diisopropyl ether in a highly efficient manner. (C) 2003 Elsevier Ltd. All rights reserved.
• Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem
  作者：Claudio Fuganti、Piero Grasselli、Monica Mendozza、Stefano Servi、Gioia Zucchi

  DOI：10.1016/s0040-4020(96)01152-0

  日期：1997.2

  (S) 2-Methoxycyclohexanone 1, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) alpha-benzylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of 1 is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into 1 through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values. (C) 1997, Elsevier Science Ltd.