2-bromo-2-(bromomethyl)succinic acid | 4167-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-bromo-2-(bromomethyl)succinic acid
• 英文别名: 2-bromo-2-bromomethylsuccinic acid；2-bromo-2-bromomethyl-succinic acid；2-Brom-2-brommethyl-bernsteinsaeure；(+/-) 2-Brom-2-brommethyl-bernsteinsaeure；2-Bromo-2-(bromomethyl)butanedioic acid
• CAS: 4167-06-0
• 化学式: C₅H₆Br₂O₄
• 分子量: 289.908
• InChiKey: YXMZDLGGYWYYLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-2-(bromomethyl)succinic acid 在 哌啶 、 sodium tetrahydroborate 、 乙酸酐 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 acetic acid 2-(5-methylfuran-2-ylmethylene)-5-oxo-2,5-dihydrofuran-3-ylmethyl ester
  参考文献：
  名称：

  A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B

  摘要：

  Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.020
• 作为产物：
  描述：

  衣康酸酐 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以98%的产率得到2-bromo-2-(bromomethyl)succinic acid
  参考文献：
  名称：

  A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B

  摘要：

  Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.020

文献信息

• A synthesis of (±)-sparteine
  作者：Thomas Buttler、Ian Fleming、Sabine Gonsior、Bo-Hye Kim、A.-Young Sung、Hee-Gweon Woo

  DOI：10.1039/b502213d

  日期：——

  ammonia. The C=C in the racemic diester 19 was ozonolysed and the diketone converted by Beckmann rearrangement into the bis-lactam . Reduction of the bis-lactam with lithium aluminium hydride and intramolecular nucleophilic displacement gave racemic sparteine 1. Some ideas for making this synthesis amenable to a synthesis of enantiomerically enriched sparteine are presented.

  在合成外消旋的斯巴地丁中，溴甲磺酸二甲酯14和二环戊烯基4之间的Diels-Alder反应，然后形成环丙烷，分别在介观中间体8中将C-1和C-5的立体化学分别设定为S和R。然后，通过用液态氨中的锂进行还原性裂解，由二酯8衍生的双烯酸酯17的中等非对映选择性质子保证了C-2和C-4的立体化学。将外消旋二酯19中的C ＝ C进行臭氧分解，并且通过贝克曼重排将二酮转化为双-内酰胺。用氢化铝锂还原双内酰胺并进行分子内亲核取代，得到外消旋的斯巴地因1。提出了一些使该合成适合对映体富集的斯巴地因的构想。
• Kekule, Justus Liebigs Annalen der Chemie, 1861, vol. Suppl.1, p. 351
  作者：Kekule

  DOI：——

  日期：——
• Morawski, Journal fur praktische Chemie (Leipzig 1954), 1875, vol. <2>11, p. 466
  作者：Morawski

  DOI：——

  日期：——
• Direct observation of reaction intermediates in debromodecarboxylation reactions
  作者：Charles A. Kingsbury

  DOI：10.1021/jo01272a045

  日期：1968.8
• Bromomesaconic and bromocitraconic acids. Potential active site labeling reagents for dicarboxylic acid metabolizing enzymes
  作者：Richard A. Laursen、Wei-Chiang Shen、Kenneth G. Zahka

  DOI：10.1021/jm00289a013

  日期：1971.7