2-(1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexa-2,5-dien-1-yl)acetic acid | 1410840-12-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexa-2,5-dien-1-yl)acetic acid
• 英文别名: 2-[1-[[Tert-butyl(diphenyl)silyl]oxymethyl]cyclohexa-2,5-dien-1-yl]acetic acid；2-[1-[[tert-butyl(diphenyl)silyl]oxymethyl]cyclohexa-2,5-dien-1-yl]acetic acid
• CAS: 1410840-12-8
• 化学式: C₂₅H₃₀O₃Si
• 分子量: 406.597
• InChiKey: QQXWDGUZNGXBDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexa-2,5-dien-1-yl)acetic acid 在 1,4-bis-(9-O-dihydroquinidinyl)phthalazine 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 1.0h， 以90%的产率得到7-bromo-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-3,3a,7,7a-tetrahydrobenzofuran-2(6H)-one
  参考文献：
  名称：

  Catalytic Desymmetrization of Cyclohexadienes by Asymmetric Bromolactonization

  摘要：

  Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.

  DOI：

  10.1021/ol302908a
• 作为产物：
  描述：

  1-Ethoxycarbonylmethyl-1-carboxy-cyclohexadien-(2,5) 在 咪唑 、 三乙胺 、 氯甲酸甲酯 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-(1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexa-2,5-dien-1-yl)acetic acid
  参考文献：
  名称：

  Catalytic Desymmetrization of Cyclohexadienes by Asymmetric Bromolactonization

  摘要：

  Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.

  DOI：

  10.1021/ol302908a

文献信息

• Catalytic Desymmetrization of Cyclohexadienes by Asymmetric Bromolactonization
  作者：Kazutada Ikeuchi、Shunsuke Ido、Satoshi Yoshimura、Tomohiro Asakawa、Makoto Inai、Yoshitaka Hamashima、Toshiyuki Kan

  DOI：10.1021/ol302908a

  日期：2012.12.7

  Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.