(R)-3,3'-bis(2-hydroxyethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthyl | 173961-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3,3'-bis(2-hydroxyethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthyl
• 英文别名: 2-[4-[3-(2-hydroxyethyl)-2-(methoxymethoxy)naphthalen-1-yl]-3-(methoxymethoxy)naphthalen-2-yl]ethanol
• CAS: 173961-77-8；350490-35-6；211560-94-0
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: DCRXVXOENQZGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-3,3'-bis(2-hydroxyethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthyl 在 potassium fluoride on basic alumina 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 (R)-4-(3-(2-allyloxyethyl)-2-benzyloxy-1-naphthyl)-3-benzyloxy-2-naphthaleneethanol
  参考文献：
  名称：

  Direct catalytic asymmetric aldol reactions promoted by novel heterobimetallic catalysts possessing strong Brønsted base: a new strategy for the development of Lewis acid–Brønsted base bifunctional catalysts

  摘要：

  Novel heterobimetallic catalysts possessing lithium alkoxide as Bronsted base have been developed. The catalysts were found to be effective in the direct asymmetric aldol reaction of less acidic dialkyl ketones as well as aromatic ketones, affording the aldol products in moderate yield and ee. Attempts at diastereo- and enantioselective direct catalytic aldol reaction of ethyl ketone using small molecule catalysts are reported for the first time. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00070-9
• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 在 正丁基锂 、 sodium hydride 作用下， 生成 (R)-3,3'-bis(2-hydroxyethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthyl
  参考文献：
  名称：

  Enantioselective trimethylsilylcyanation of aldehydes catalyzed by chiral lanthanoid alkoxides

  摘要：

  首次实现了由手性联萘酚和联萘酚改性镧烷氧化物催化醛的对映选择性三甲基硅基氰化反应，其中观察到BINOL 3,3′-位上的取代基对对映选择性有明显的影响，并且3,3′-双(甲氧基乙基)-BINOL比简单的BINOL具有优势，能够以73%的ee产生高产率的(S)-产物。

  DOI：

  10.1039/a802509f

文献信息

• Li, Jing; Li, Weidong; Li, Ying, Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 685 - 690
  作者：Li, Jing、Li, Weidong、Li, Ying、Li, Yulin、Yang, Shiyan

  DOI：——

  日期：——
• Stereoselective conjugate addition of diethylzinc to enones and nitroalkenes
  作者：Jahyo Kang、Jae Hoon Lee、Dae Sung Lim

  DOI：10.1016/s0957-4166(02)00838-8

  日期：2003.2

  Bidirectionally directed conjugate addition of diethylzinc to enones and nitroalkene was achieved with good enantioselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Qian, Changtao; Huang, Taisheng; Zhu, Chengjian, Journal of the Chemical Society. Perkin transactions I, 1998, # 13, p. 2097 - 2103
  作者：Qian, Changtao、Huang, Taisheng、Zhu, Chengjian、Sun, Jie

  DOI：——

  日期：——
• Direct catalytic asymmetric aldol reactions promoted by novel heterobimetallic catalysts possessing strong Brønsted base: a new strategy for the development of Lewis acid–Brønsted base bifunctional catalysts
  作者：Naoki Yoshikawa、Masakatsu Shibasaki

  DOI：10.1016/s0040-4020(01)00070-9

  日期：2001.3

  Novel heterobimetallic catalysts possessing lithium alkoxide as Bronsted base have been developed. The catalysts were found to be effective in the direct asymmetric aldol reaction of less acidic dialkyl ketones as well as aromatic ketones, affording the aldol products in moderate yield and ee. Attempts at diastereo- and enantioselective direct catalytic aldol reaction of ethyl ketone using small molecule catalysts are reported for the first time. (C) 2001 Published by Elsevier Science Ltd.
• Enantioselective trimethylsilylcyanation of aldehydes catalyzed by chiral lanthanoid alkoxides
  作者：Changtao Qian、Chengjian Zhu、Taisheng Huang

  DOI：10.1039/a802509f

  日期：——

  The first example of enantioselective trimethylsilylcyanation of aldehydes catalyzed by chiral binaphthol and binaphthol-modified lanthanum alkoxides has been achieved, in which an obvious effect of substituents at the 3,3′-positions of BINOL on the enantioselectivity was observed and 3,3′-bis(methoxyethyl)-BINOL had the advantage over simple BINOL to give (S)-products in excellent yields with 73% ee.

  首次实现了由手性联萘酚和联萘酚改性镧烷氧化物催化醛的对映选择性三甲基硅基氰化反应，其中观察到BINOL 3,3′-位上的取代基对对映选择性有明显的影响，并且3,3′-双(甲氧基乙基)-BINOL比简单的BINOL具有优势，能够以73%的ee产生高产率的(S)-产物。