(1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol | 1268519-04-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol
• CAS: 1268519-04-5
• 化学式: C₁₄H₁₀Br₄O₂
• 分子量: 529.848
• InChiKey: AKTHDXSDWPVBNY-ZIAGYGMSSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  558.5±45.0 °C(Predicted)
• 密度：
  2.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 四(三苯基膦)钯 、 氯化亚砜 、 三氟化硼乙醚 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 69.0h， 生成 (2R,3R)-1,1-bis(chloromethyl)-2,3-bis(3',5'-diphenylphenyl)cyclopropane
  参考文献：
  名称：

  A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids

  摘要：

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.10.027
• 作为产物：
  描述：

  (3,5-二溴苄基)磷酸二乙酯 在 甲基磺酰胺 、 potassium tert-butylate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 123.0h， 生成 (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol
  参考文献：
  名称：

  A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids

  摘要：

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.10.027
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以49%的产率得到(R)-(+)-1-苯基-1-丙醇
  参考文献：
  名称：

  C 2对称手性二醇催化二乙基锌向芳香醛的对映选择性加成

  摘要：

  光学纯的C 2对称二醇已经以直接的方式以中等产率合成，并且在芳族醛与二乙基锌的对映选择性烷基化中用作催化剂。在（1 R，2 R）-1,2-双（3,5-二溴苯基）-乙烷- 1,2-二醇和（1 R，2 R）-1,2-双（3,5-二苯基苯基）-乙烷-1,2-二醇。

  DOI：

  10.1016/j.tetlet.2014.03.058

文献信息

• Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by C2-symmetric chiral diols
  作者：Yaşar Gök、Levent Kekeç

  DOI：10.1016/j.tetlet.2014.03.058

  日期：2014.4

  Optically pure C2-symmetric diols have been synthesized with moderate yields in a straightforward manner, and are used as catalysts in the enantioselective alkylation of aromatic aldehydes with diethylzinc. The addition of diethylzinc to benzaldehyde and sterically hindered 1-naphthaldehyde was achieved with excellent enantioselectivities (97–99% ee) under catalysis with (1R,2R)-1,2-bis(3,5-dibromophenyl)-ethane-1

  光学纯的C 2对称二醇已经以直接的方式以中等产率合成，并且在芳族醛与二乙基锌的对映选择性烷基化中用作催化剂。在（1 R，2 R）-1,2-双（3,5-二溴苯基）-乙烷- 1,2-二醇和（1 R，2 R）-1,2-双（3,5-二苯基苯基）-乙烷-1,2-二醇。
• A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids
  作者：Yaşar Gök、Timothy Noël、Johan Van der Eycken

  DOI：10.1016/j.tetasy.2010.10.027

  日期：2010.12

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.