(S)-1,1-bis(phenylsulfonyl)-3-(1-methoxy-1-methylethyl)-4-methylenecyclopentane | 1207378-60-6

• 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: (S)-1,1-bis(phenylsulfonyl)-3-(1-methoxy-1-methylethyl)-4-methylenecyclopentane
• 英文别名: [(3S)-1-(benzenesulfonyl)-3-(2-methoxypropan-2-yl)-4-methylidenecyclopentyl]sulfonylbenzene
• CAS: 1207378-60-6
• 化学式: C₂₂H₂₆O₅S₂
• 分子量: 434.577
• InChiKey: CMOOABBWELSJMA-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 4,4-bis(phenylsulfonyl)-7-methyl-6-octen-1-yne 在 C₅₇H₃₆AuClN₂ 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 二氯甲烷 为溶剂， 反应 88.0h， 生成 (S)-1,1-bis(phenylsulfonyl)-3-(1-methoxy-1-methylethyl)-4-methylenecyclopentane 、 (S)-1,1-bis(phenylsulfonyl)-3-(1-methoxy-1-methylethyl)-4-methylenecyclopentane
  参考文献：
  名称：

  Synthesis of a New Chiral C2-Symmetric NHC-AuCl Complex

  摘要：

  A New chiral C-2 symmetric NHC ligand with two binaphthyl units has been synthesized. The new NHC ligand features two seven-membered rings that link the imidazolylidene with the binaphthyl units. X-Ray crystallographic analysis of the new NHC-AuCl complex indicates that the Au-Cl bond is located between the phenyl groups of the binaphthyl units and suggests that this arrangement could induce enantioselectivity in reactions. Indeed, catalytic asymmetric ene-yne cyclization of 2b in the presence of a catalytic amount (5 mol%) of cationic complex of 13 quantitatively afforded the cyclized product with 78% ee.

  DOI：

  10.3987/com-16-13408

文献信息

• Steric tuning of C2-symmetric chiral N-heterocyclic carbene in gold-catalyzed asymmetric cyclization of 1,6-enynes
  作者：Ken-ichi Yamada、Yasumasa Matsumoto、Khalid B. Selim、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2012.03.107

  日期：2012.6

  Steric tuning of C2-symmetric chiral N-heterocyclic carbene (NHC) was performed in Au(I)-catalyzed asymmetric cyclization of 1,6-enyne. Higher enantioselectivity was realized when chiral NHC–AuCl/AgSbF6 catalysts whose N-substituent on the NHC overlays the Au–Cl bond was utilized.

  在Au（I）催化的1,6-烯炔的不对称环化反应中，对C 2对称的手性N杂环卡宾（NHC）进行了立体调节。当使用手性NHC-AuCl / AgSbF 6催化剂（其在NHC上的N-取代物覆盖Au-Cl键）时，实现了更高的对映选择性。
• Chiral carbene approach to gold-catalyzed asymmetric cyclization of 1,6-enynes
  作者：Yasumasa Matsumoto、Khalid B. Selim、Hirotsugu Nakanishi、Ken-ichi Yamada、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1016/j.tetlet.2009.11.039

  日期：2010.1

  Chiral C-2-symmetric N-heterocyclic carbenes (NHCs) were tested for their stereocontrolling abilities in gold(I)-catalyzed asymmetric cyclization of 1,6-enynes giving the corresponding cyclopentane derivatives with moderate enantioselectivity of up to 59%. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a New Chiral C2-Symmetric NHC-AuCl Complex
  作者：Masahisa Nakada、Naoya Okitsu、Takuya Yoshida、Kensuke Usui

  DOI：10.3987/com-16-13408

  日期：——

  A New chiral C-2 symmetric NHC ligand with two binaphthyl units has been synthesized. The new NHC ligand features two seven-membered rings that link the imidazolylidene with the binaphthyl units. X-Ray crystallographic analysis of the new NHC-AuCl complex indicates that the Au-Cl bond is located between the phenyl groups of the binaphthyl units and suggests that this arrangement could induce enantioselectivity in reactions. Indeed, catalytic asymmetric ene-yne cyclization of 2b in the presence of a catalytic amount (5 mol%) of cationic complex of 13 quantitatively afforded the cyclized product with 78% ee.