(-)-tris([1R,2S,5R]-menthyl)tin chloride | 182160-41-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-tris([1R,2S,5R]-menthyl)tin chloride
• 英文别名: tri-(-)-menthyltin chloride；tri(-)menthyltin chloride；Chlorotris[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]stannane；chloro-tris[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]stannane
• CAS: 182160-41-4
• 化学式: C₃₀H₅₇ClSn
• 分子量: 571.946
• InChiKey: KRQBWVGIKRMSRD-JGQWCBKCSA-M

物化性质

• 熔点：
  80-81 °C(Solv: ethanol (64-17-5))
• 沸点：
  527.4±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.56
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  potassium fluoride 、 (-)-tris([1R,2S,5R]-menthyl)tin chloride 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到(-)-tris([1R,2S,5R]-menthyl)tin fluoride
  参考文献：
  名称：

  The First Dimeric Triorganotin Fluoride:  Stabilization by Unsymmetrically Oriented Menthyl Substituents

  摘要：

  In the solid state, (-)-tris([1R,2S,5R]-menthyl)tin fluoride, Men(3)SnF (6), exhibits a dimeric structure in which one tin atom is four-coordinate and the other five-coordinate. This novel dimeric association mode is attributed to the orientation of the unsymmetrical menthyl groups, which are arranged to allow a minimum (SnSn)-Sn-... separation of 4.84 Angstrom within the dimer. The exocyclic isopropyl groups of the menthyl groups point in opposite directions on each tin atom of the dimer, thus preventing further association ((SnSn)-Sn-... separation outside the dimer 10.49 Angstrom). Sn-119 and F-19 MAS NMR spectroscopy were utilized to probe the diverse coordination numbers found by X-ray crystallography for the geometries of the two tin and fluorine sites. In solution, 6 is a monomer at both room temperature and -100degreesC. However, upon addition of Bu4NF, 6 is in equilibrium with [(Men3SnF)(2)F](-) (6a), [Men(3)SnF(2)](-) (6b), and noncoordinating fluoride anions.

  DOI：

  10.1021/om049140y
• 作为产物：
  描述：

  盐酸 、 氯代薄荷脑 、 四氯化锡 在 magnesium 作用下， 以 not given 为溶剂， 生成 (-)-tris([1R,2S,5R]-menthyl)tin chloride
  参考文献：
  名称：

  用于多相双金属催化的新型光学活性有机锡化合物

  摘要：

  具有与金属（-）-Ment 2 SnMe 2，（-）-Ment 2 SnPh 2，（-）-Ment 3 SnCl，（-）-Ment 3 SnH ，金属相邻的两个或三个手性中心的手性锡（IV）衍生物；（-）-（1R，2S，5R）-1-氯-5-甲基-2-异丙基环己烷，R 2 Sn [CH（Me）（n-Hex）] 2（RBu或Ph）已被通过将甲基氯化镁与卤化锡偶合或通过锡酸锂与光学活性（2-辛基）甲苯磺酸酯的反应制备。两种方法的立体特异性都很高，从而导致了新的光学纯有机锡试剂已被充分表征。

  DOI：

  10.1016/0022-328x(96)06270-5

文献信息

• Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
  作者：Virginia Vetere、María B. Faraoni、Julio C. Podestá、Mónica L. Casella

  DOI：10.1016/j.apcata.2012.08.031

  日期：2012.11

  In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (-)-menthyl group: (-)-Pt-MenSnBu(3) and (-)-Men(3)Sn-Sn-(-)-Men(3). The organotin chiral modifiers were carefully synthesized and characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transition metal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25-27% for 4-hydroxy-3-hexanone. (C) 2012 Elsevier B.V. All rights reserved.
• The First Dimeric Triorganotin Fluoride:  Stabilization by Unsymmetrically Oriented Menthyl Substituents
  作者：Jens Beckmann、Dainis Dakternieks、Andrew Duthie

  DOI：10.1021/om049140y

  日期：2005.2.1

  In the solid state, (-)-tris([1R,2S,5R]-menthyl)tin fluoride, Men(3)SnF (6), exhibits a dimeric structure in which one tin atom is four-coordinate and the other five-coordinate. This novel dimeric association mode is attributed to the orientation of the unsymmetrical menthyl groups, which are arranged to allow a minimum (SnSn)-Sn-... separation of 4.84 Angstrom within the dimer. The exocyclic isopropyl groups of the menthyl groups point in opposite directions on each tin atom of the dimer, thus preventing further association ((SnSn)-Sn-... separation outside the dimer 10.49 Angstrom). Sn-119 and F-19 MAS NMR spectroscopy were utilized to probe the diverse coordination numbers found by X-ray crystallography for the geometries of the two tin and fluorine sites. In solution, 6 is a monomer at both room temperature and -100degreesC. However, upon addition of Bu4NF, 6 is in equilibrium with [(Men3SnF)(2)F](-) (6a), [Men(3)SnF(2)](-) (6b), and noncoordinating fluoride anions.
• New optically active organotin compounds for heterogeneous bimetallic catalysis
  作者：Christine Lucas、Catherine C. Santini、Martina Prinz、Marie-Anne Cordonnier、Jean-Marie Basset、Marie-Françoise Connil、Bernard Jousseaume

  DOI：10.1016/0022-328x(96)06270-5

  日期：1996.8

  Chiral tin(IV) derivatives with two or three chiral centers adjacent to the metal (−)-Ment2SnMe2, (−)-Ment2SnPh2, (−)-Ment3 SnCl, (−)-Ment3SnH; (−)-Ment  (1R, 2S, 5R)-1-chloro-5-methyl-2-isopropylcyclohexane, R2Sn[CH(Me)(n-Hex)]2 (R  Bu or Ph) have been prepared either by the coupling of methylmagnesium chloride with tin halides or by the reaction of lithium stannates with optically active (2-octyl)tosylate

  具有与金属（-）-Ment 2 SnMe 2，（-）-Ment 2 SnPh 2，（-）-Ment 3 SnCl，（-）-Ment 3 SnH ，金属相邻的两个或三个手性中心的手性锡（IV）衍生物；（-）-（1R，2S，5R）-1-氯-5-甲基-2-异丙基环己烷，R 2 Sn [CH（Me）（n-Hex）] 2（RBu或Ph）已被通过将甲基氯化镁与卤化锡偶合或通过锡酸锂与光学活性（2-辛基）甲苯磺酸酯的反应制备。两种方法的立体特异性都很高，从而导致了新的光学纯有机锡试剂已被充分表征。