(4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide | 1268519-05-6

• 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: (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide
• 英文别名: (4R,5R)-4,5-bis(3,5-dibromophenyl)-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 1268519-05-6
• 化学式: C₁₄H₈Br₄O₄S
• 分子量: 591.897
• InChiKey: QHAMBYBSJYCFMX-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide 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 62.0h， 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 氯化亚砜 、 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 、 四氯化碳 、 水 、 叔丁醇 为溶剂， 反应 130.0h， 生成 (4R,5R)-4,5-bis(3',5'-dibromophenyl)-(1,3,2)-dioxathiolane-2,2-dioxide
  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

文献信息

• 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.