(S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene | 319924-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene
• 英文别名: 2,4-dibromo-1-[(1S)-3-chloro-1-phenylpropoxy]benzene
• CAS: 319924-81-7
• 化学式: C₁₅H₁₃Br₂ClO
• 分子量: 404.529
• InChiKey: XTNLMXXPJKNWJN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以79%的产率得到(S)-8-bromo-3,4-dihydro-2-phenyl-2H-1-benzopyran
  参考文献：
  名称：

  Inter- and intramolecular Mitsunobu reaction based approaches to 2-substituted chromans and chroman-4-ones

  摘要：

  Two approaches to optically active 2-substituted chromans and chrornan-4-ones are described. The first utilized an intermolecular Mitsunobu reaction of a homochiral halopropanol and 2-bromophenol followed by cyclization to the 2-substituted chroman. In addition, a double lithiation procedure was developed to introduce additional functionality to the chroman. The second approach utilized an intramolecular Mitsunobu cyclization to give the 2-substituted chroman-4-one nucleus. The methodologies were applied to the syntheses of several biologically active natural and synthetic products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.047
• 作为产物：
  描述：

  2,4-二溴苯酚 、 (R)-(+)-3-氯-1-苯基-1-丙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到(S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene
  参考文献：
  名称：

  Inter- and intramolecular Mitsunobu reaction based approaches to 2-substituted chromans and chroman-4-ones

  摘要：

  Two approaches to optically active 2-substituted chromans and chrornan-4-ones are described. The first utilized an intermolecular Mitsunobu reaction of a homochiral halopropanol and 2-bromophenol followed by cyclization to the 2-substituted chroman. In addition, a double lithiation procedure was developed to introduce additional functionality to the chroman. The second approach utilized an intramolecular Mitsunobu cyclization to give the 2-substituted chroman-4-one nucleus. The methodologies were applied to the syntheses of several biologically active natural and synthetic products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.047

文献信息

• A stereocontrolled route to 2-substituted chromans
  作者：Kevin J Hodgetts

  DOI：10.1016/s0040-4039(00)01530-6

  日期：2000.10

  A two-step synthesis of 2-substituted chromans of high enantiomeric purity is described. Mitsunobu reaction of homochiral halopropanols 10 with 2-bromophenol (9), followed by treatment with n-butyllithium under Parham cycloalkylation conditions generates 2-substituted chromans 7. The methodology was applied to the synthesis of the natural product tephrowatsin E (5) and the antiviral BW683C (6).

  描述了两步合成高对映体纯度的2-取代的苯并二氢吡喃。同手性卤代丙醇10与2-溴苯酚（9）的Mitsunobu反应，然后在Parham环烷基化条件下用正丁基锂处理，生成2-取代的苯并吡喃7。该方法学适用于合成天然产物妥罗维他命E（5）和抗病毒BW683C（6）。