(1R,2S)-2-(trityloxymethyl)cyclopropanemethanol | 142185-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1R,2S)-2-(trityloxymethyl)cyclopropanemethanol
• 英文别名: (2R,3S)-4-trityloxy-2,3-methano-1-butanol；(2R,3S)-cis-4-trityloxy-2,3-methanobutan-1-ol；[(1R,2S)-2-(trityloxymethyl)cyclopropyl]methanol
• CAS: 142185-63-5
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: RIGYXNSQLNSSFL-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(trityloxymethyl)cyclopropanemethanol 在 chromium(VI) oxide 、 四溴化碳 、 硫酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 43.67h， 生成 (3S,4R)-N-t-butoxycarbonyl-3,4-methano-2-pyrrolidone
  参考文献：
  名称：

  Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

  摘要：

  A series of cyclopropane-based conformationally restricted gamma-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4-methano analogs IIa and IIb and their enantiomers ent-IIa and ent-Iib, were synthesized from the chiral cyclopropane units Type-a and Type-b that we developed. These analogs were systematically evaluated with four GABA transporter (GAT) subtypes. The trans-3,4-methano analog IIa had inhibitory effects on GAT3 (IC50 = 23.9 mu M) and betaine-GABA transporter1 (5.48 mu M), indicating its potential as an effective lead compound for the development of potent GAT inhibitors due to its hydrophilic and low molecular weight properties and excellent ligand efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.063
• 作为产物：
  描述：

  (1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 (1R,2S)-2-(trityloxymethyl)cyclopropanemethanol
  参考文献：
  名称：

  Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

  摘要：

  A series of cyclopropane-based conformationally restricted gamma-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4-methano analogs IIa and IIb and their enantiomers ent-IIa and ent-Iib, were synthesized from the chiral cyclopropane units Type-a and Type-b that we developed. These analogs were systematically evaluated with four GABA transporter (GAT) subtypes. The trans-3,4-methano analog IIa had inhibitory effects on GAT3 (IC50 = 23.9 mu M) and betaine-GABA transporter1 (5.48 mu M), indicating its potential as an effective lead compound for the development of potent GAT inhibitors due to its hydrophilic and low molecular weight properties and excellent ligand efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.063

文献信息

• <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetraalkyl-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxamides: Novel Chiral Auxiliaries for Asymmetric Simmons–Smith Cyclopropanation of Allylic Alcohols and for Asymmetric Diethylzinc Addition to Aldehydes
  作者：Hiroshi Kitajima、Katsuji Ito、Yuko Aoki、Tsutomu Katsuki

  DOI：10.1246/bcsj.70.207

  日期：1997.1

  efficient chiral auxiliaries for the asymmetric Simmons–Smith cyclopropanation of allylic alcohols and for asymmetric addition of diethylzinc to aldehydes. For example, Simmons-Smith cyclopropanation of cinnamyl alcohol in the presence of N,N,N′,N′-tetraethyl-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxamide (1b) proceeded with high enantioselectivity of 94% ee and addition of diethylzinc to benzaldehyde

  发现新引入的标题化合物是烯丙醇的不对称 Simmons-Smith 环丙烷化和二乙基锌与醛的不对称加成的有效手性助剂。例如，在 N,N,N',N'-tetraethyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamide (1b) 存在下肉桂醇的 Simmons-Smith 环丙烷化反应进行在 N,N,N',N'-四异丙基-2,2'-二羟基-1,1'-联萘-3,3'-二甲酰胺存在下，具有 94% ee 的高对映选择性和二乙基锌与苯甲醛的加成（ 1e) 以 99% ee 的对映选择性进行。尽管这些反应的反应机理仍然是核反应，但单体七元 2,2'-二羟基-1,1'-联萘-3,3'-二甲酰胺 (1)-Zn 复合物被认为是一种活性物质，催化上述反应，
• A catalytic enantioselective reaction using a C-symmetric disulfonamide as a chiral ligand: Simmons-Smith cyclopropanation of allylic alcohols by the Et2Zn-CH2I2-disulfonamide system
  作者：Hideyo Takahashi、Masato Yoshioka、Masakatsu Shibasaki、Masaji Ohno、Nobuyuki Imai、Susumu Kobayashi

  DOI：10.1016/0040-4020(95)00760-6

  日期：1995.10

  A catalytic and enantioselective Simmons-Smith Cyclopropanation of an allylic alcohol was developed by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 4.

  在催化量的手性二磺酰胺4的存在下，通过烯丙基醇与Et 2 Zn和CH 2 I 2的反应，开发了烯丙基醇的催化和对映选择性席梦思-史密斯环丙烷化反应。
• Asymmetric Simmons-Smith Cyclopropanation of<i>E</i>-Allylic Alcohols Using 1,1′-Bi-2-naphthol-3,3′-dicarboxamide as a Chiral Auxiliary
  作者：Hiroshi Kitajima、Yuko Aoki、Katsuji Ito、Tsutomu Katsuki

  DOI：10.1246/cl.1995.1113

  日期：1995.12

  N,N,N′,N′-Tetraethyl-1,1′-bi-2-naphthol-3,3′-dicarboxamide (1b) was found to be an effective chiral auxiliary for asymmetric Simmons-Smith cyclopropanation and high enantioselectivity greater than 85% ee was achieved in the reaction of E-allylic alcohols.

  N,N,N',N'-Tetraethyl-1,1'-bi-2-naphthol-3,3'-dicarboxamide (1b) 被发现是一种有效的手性助剂，可用于不对称 Simmons-Smith 环丙烷化和更高的对映选择性E-烯丙醇的反应达到了85%以上的ee。
• Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols
  作者：Yuya Kawashima、Tetsuya Ezawa、Mai Yamamura、Taisuke Harada、Takuya Noguchi、Tsuyoshi Miura、Nobuyuki Imai

  DOI：10.1016/j.tet.2015.09.024

  日期：2015.11

  Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
• A catalytic enantioselective reaction using a C2-symmetric disulfonamide as a chiral ligand: cyclopropanation of allylic alcohols by the Et2Zn-CH2I2-disulfonamide system
  作者：Hideyo Takahashi、Masato Yoshioka、Masaji Ohno、Susumu Kobayashi

  DOI：10.1016/s0040-4039(00)92246-9

  日期：1992.4

  The first catalytic, enantioselective Simmons-Smith cyclopropanation of an allylic alcohol has been achieved by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 1.