(S)-2-methyl-acrylic acid 8-(2,2'-dihydroxy-1,1'-binaphth-6-yl)octyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-methyl-acrylic acid 8-(2,2'-dihydroxy-1,1'-binaphth-6-yl)octyl ester
• 英文别名: 8-[6-Hydroxy-5-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl]octyl 2-methylprop-2-enoate；8-[6-hydroxy-5-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl]octyl 2-methylprop-2-enoate
• 化学式: C₃₂H₃₄O₄
• 分子量: 482.62
• InChiKey: ASAXGJVOWRQJNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-acrylic acid 8-(2,2'-dihydroxy-1,1'-binaphth-6-yl)octyl ester 在 三乙胺 、 三氯氧磷 、 sodium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以91%的产率得到Sodium;8-(13-oxido-13-oxo-12,14-dioxa-13lambda5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),4,6,9,16,18,20,22-decaen-6-yl)octyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Development of new methods toward efficient immobilization of chiral catalysts

  摘要：

  BINOL moieties are efficiently immobilized onto the surface of a micelle-derived spherical polymer and a monolayer-protected Au cluster (Au-MPC). Ti-BINOLate complexes generated from the BINOL immobilized polymer and Au-MPC are found to promote catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 84% ee and 86% ee, respectively. Au-MPC-supported multicomponent asymmetric catalyst was prepared and used in the Michael reaction of 2-cyclohexen- 1-one with dibenzyl malonate affording the adduct in up to 67% yield and 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.018
• 作为产物：
  描述：

  7-溴庚酸乙酯 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 氢气 、 sodium ethanolate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 65.0h， 生成 (S)-2-methyl-acrylic acid 8-(2,2'-dihydroxy-1,1'-binaphth-6-yl)octyl ester
  参考文献：
  名称：

  Development of new methods toward efficient immobilization of chiral catalysts

  摘要：

  BINOL moieties are efficiently immobilized onto the surface of a micelle-derived spherical polymer and a monolayer-protected Au cluster (Au-MPC). Ti-BINOLate complexes generated from the BINOL immobilized polymer and Au-MPC are found to promote catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 84% ee and 86% ee, respectively. Au-MPC-supported multicomponent asymmetric catalyst was prepared and used in the Michael reaction of 2-cyclohexen- 1-one with dibenzyl malonate affording the adduct in up to 67% yield and 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.018

文献信息

• Micelle-derived polymer supports for enantioselective catalysts
  作者：Shinobu Takizawa、Mahesh L. Patil、Fumiko Yonezawa、Kazuyoshi Marubayashi、Hiroyuki Tanaka、Tomoji Kawai、Hiroaki Sasai

  DOI：10.1016/j.tetlet.2004.12.051

  日期：2005.2

  The BINOL moieties are successfully immobilized on the surface of a micelle-derived polymer. Ti-BINOLate complexes prepared from the polymer with Ti(O-i-Pr)(4) exhibited high catalytic activity for the asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 96% yield with 84% ee. (C) 2004 Elsevier Ltd. All rights reserved.