(2R,3R)-1,4-dibromobutane-2,3-diol | 15410-44-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3R)-1,4-dibromobutane-2,3-diol
• 英文别名: (R,R)-1,4-dibromo-butane-2,3-diol；1,4-dibromo-L-1,4-dideoxy-threitol；(2S,3S)-1,4-Dibrom-butan-2,3-diol；(L)-(+)-1,4-Dibromo-2,3-butanediol
• CAS: 15410-44-3
• 化学式: C₄H₈Br₂O₂
• 分子量: 247.914
• InChiKey: XOWDQAHYPSENAC-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  N-丁基咪唑 、 (2R,3R)-1,4-dibromobutane-2,3-diol 以 甲苯 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  咪唑基手性离子液体的合成与应用

  摘要：

  的含有咪唑核和手性中心的手性离子液体的合成ñ -取代基被报告。[（2小号，3小号）-2,3- Dihydroxybutane -1,4-双（3-丁基咪唑）] - [双（三氟甲磺酰）酰胺] 2和[（4-小号，5小号）-2-苯基-1- 1,3-二氧戊环-4,5-二（1-甲基咪唑）] - [双（三氟甲磺酰）酰胺] 2在迈克尔加成丙二酸酯的查耳酮向诱导对映选择性。

  DOI：

  10.1016/j.tet.2013.09.017
• 作为产物：
  描述：

  (2R)-2-[(2R)-环氧乙烷-2-基]环氧乙烷 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 (2R,3R)-1,4-dibromobutane-2,3-diol
  参考文献：
  名称：

  Feit,P.W., Chemische Berichte, 1960, vol. 93, p. 116 - 127

  摘要：

  DOI：

文献信息

• Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from l-tartrate
  作者：Shigeru Arai、Riichiro Tsuji、Atsushi Nishida

  DOI：10.1016/s0040-4039(02)02415-2

  日期：2002.12

  The catalytic asymmetric Michael reaction of a glycine Schiff base was demonstrated using new PTCs and moderate to good ee's were achieved (up to 77% ee).

  使用新的PTCs证明了甘氨酸席夫碱的催化不对称迈克尔反应，并实现了中等至良好的ee（高达ee的77％）。
• <i>C</i>₂-Symmetrical 3,4-Ethylenedioxythiophene Monomers through a Divergent Approach
  作者：Angelo Martinelli、Andrea Nitti、Riccardo Po、Dario Pasini

  DOI：10.1021/acs.joc.3c02972

  日期：2024.3.15

  ene (EDOT) monomers in which functionalities can be introduced as pendant chains from the ethylene bridge. The key synthon, obtained through a high yielding trans-etherification, is the chiral EDOT with bromomethyl pendant groups and is prone to substitution reactions with oxygen-based nucleophiles. Elimination of the key precursor affords a diene that can be elaborated into unprecedented PhEDOT monomers

  我们提出了一种C 2对称 3,4-乙撑二氧噻吩 (EDOT) 单体的不同合成方法，其中功能可以作为乙烯桥的侧链引入。通过高产率的醚交换反应获得的关键合成子是带有溴甲基侧基的手性 EDOT，并且易于与氧基亲核试剂发生取代反应。消除关键的前体得到了一种二烯，可以使用狄尔斯-阿尔德反应将其精细加工成前所未有的 PhEDOT 单体。该策略通过含二噻烷的 EDOT 的合成得到进一步验证。
• Stereoisomere 1,4-Di-O-methansulfonyl-butan-1,2,3,4-tetrole
  作者：P.W. Feit

  DOI：10.1016/s0040-4039(01)91680-6

  日期：1961.1
• In Vitro Metabolism of Chloroprene:  Species Differences, Epoxide Stereochemistry and a De-chlorination Pathway
  作者：Lisa Cottrell、Bernard T. Golding、Tony Munter、William P. Watson

  DOI：10.1021/tx0155404

  日期：2001.11.1

  Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.
• 1,4-Bismethanesulfonates of the Stereoisomeric Butanetetraols and Related Compounds
  作者：Peter W. Feit

  DOI：10.1021/jm00331a004

  日期：1964.1