3-bromo-8b-(((tert-butyldiphenylsilyl)oxy)methyl)-2a,3,4,8b-tetrahydro-1H-naphtho[2,1-b]oxet-1-one | 1410840-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-bromo-8b-(((tert-butyldiphenylsilyl)oxy)methyl)-2a,3,4,8b-tetrahydro-1H-naphtho[2,1-b]oxet-1-one
• 英文别名: (2aS,3S,8bR)-3-bromo-8b-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2aH-naphtho[2,1-b]oxet-1-one
• CAS: 1410840-24-2
• 化学式: C₂₈H₂₉BrO₃Si
• 分子量: 521.526
• InChiKey: DTSVTRVVQNWNEH-OARDWFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-二氢-1-萘甲酸 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 氨 、 lithium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.83h， 生成 1-(((tert-butyldiphenylsilyl)oxy)methyl)-1,4-dihydronaphthalene-1-carboxylic acid 、 1-(((tert-butyldiphenylsilyl)oxy)methyl)-1,4-dihydronaphthalene-1-carboxylic acid 、 3-bromo-8b-(((tert-butyldiphenylsilyl)oxy)methyl)-2a,3,4,8b-tetrahydro-1H-naphtho[2,1-b]oxet-1-one 、 3-bromo-8b-(((tert-butyldiphenylsilyl)oxy)methyl)-2a,3,4,8b-tetrahydro-1H-naphtho[2,1-b]oxet-1-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

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.