(R,R)-1-amino-2-(diphenylphosphino)cyclohexane D-tartrate | 804523-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,R)-1-amino-2-(diphenylphosphino)cyclohexane D-tartrate
• 英文别名: (R,R)-1-amino-2-diphenylphosphino D-tartrate；[(1R,2R)-2-diphenylphosphanylcyclohexyl]azanium;(2S,3S)-2,3,4-trihydroxy-4-oxobutanoate
• CAS: 804523-57-7
• 化学式: C₄H₆O₆*C₁₈H₂₂NP
• 分子量: 433.441
• InChiKey: BXCMLXABBWDFSW-JAQNTHGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  邻甲基苄醇 、 (R,R)-1-amino-2-(diphenylphosphino)cyclohexane D-tartrate 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以88%的产率得到trans-N-(2'-hydroxobenzylidene)-1-amino-2-diphenylphosphino cyclohexane
  参考文献：
  名称：

  Aziridine-derived iminophosphine ligands in palladium-catalyzed allylic substitution

  摘要：

  New iminophosphines have been synthesized from (R,R)-1-amino-2-diphenylphosphino cyclohexane (R.R)-1 in good to excellent yields. The catalysts obtained from iminophosphines 3a-g and [Pd(C3H5)Cl](2) promote the enantioselective allylic substitution of 1,3-diphenyl-2-propenyl acetate (6) with diethyl malonate with good enantioselectivity. The air-stable complex PdCl2[K-2-P,N-(R,R)-2-Ph2PC6H10N=CHPh] (4) has been prepared and structurally characterized by X-ray crystallography. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.07.066
• 作为产物：
  描述：

  D-酒石酸 、 (1R,2R)-(-)-2-(二苯基膦基)环己基胺,97+ 以 水 为溶剂， 以1.81 g的产率得到(R,R)-1-amino-2-(diphenylphosphino)cyclohexane D-tartrate
  参考文献：
  名称：

  芳香醛与甲基乙烯基酮的对映选择性森田-贝利斯-希尔曼反应中的手性膦硫脲有机催化剂

  摘要：

  新型的手性膦硫脲已被开发为有效的有机催化剂，用于芳香醛与甲基乙烯基酮的对映选择性Morita-Baylis-Hillman反应。反应在非常温和的条件下进行，可以在短时间内以高达94％ee的良好收率获得所需的产物。

  DOI：

  10.1016/j.tetlet.2008.08.042

文献信息

• Aziridine-derived iminophosphine ligands in palladium-catalyzed allylic substitution
  作者：Shadi Dalili、Aldo Caiazzo、Andrei K. Yudin

  DOI：10.1016/j.jorganchem.2004.07.066

  日期：2004.11

  New iminophosphines have been synthesized from (R,R)-1-amino-2-diphenylphosphino cyclohexane (R.R)-1 in good to excellent yields. The catalysts obtained from iminophosphines 3a-g and [Pd(C3H5)Cl](2) promote the enantioselective allylic substitution of 1,3-diphenyl-2-propenyl acetate (6) with diethyl malonate with good enantioselectivity. The air-stable complex PdCl2[K-2-P,N-(R,R)-2-Ph2PC6H10N=CHPh] (4) has been prepared and structurally characterized by X-ray crystallography. (C) 2004 Elsevier B.V. All rights reserved.
• Chiral phosphinothiourea organocatalyst in the enantioselective Morita–Baylis–Hillman reactions of aromatic aldehydes with methyl vinyl ketone
  作者：Kui Yuan、Lei Zhang、Hong-Liang Song、Yinjun Hu、Xin-Yan Wu

  DOI：10.1016/j.tetlet.2008.08.042

  日期：2008.10

  A new class of chiral phosphinothioureas has been developed as efficient organocatalyst for the enantioselective Morita–Baylis–Hillman reaction of aromatic aldehydes with methyl vinyl ketone. The reaction proceeds under very mild conditions to afford the desired product in a short time period in good to excellent yields with up to 94% ee.

  新型的手性膦硫脲已被开发为有效的有机催化剂，用于芳香醛与甲基乙烯基酮的对映选择性Morita-Baylis-Hillman反应。反应在非常温和的条件下进行，可以在短时间内以高达94％ee的良好收率获得所需的产物。