(1R,2S,5R,6R)-3-bromo-5,6-dimethoxycyclohex-3-ene-1,2-diol | 1514823-92-7

• 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: (1R,2S,5R,6R)-3-bromo-5,6-dimethoxycyclohex-3-ene-1,2-diol
• CAS: 1514823-92-7
• 化学式: C₈H₁₃BrO₄
• 分子量: 253.093
• InChiKey: KSLYAJWJGLALEI-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R,6R)-3-bromo-5,6-dimethoxycyclohex-3-ene-1,2-diol 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 草酰氯 、 zinc(II) acetate dihydrate 、 二异丁基氢化铝 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 51.66h， 生成 (2S,3R,4R)-4-hydroxy-6-isopropoxy-2,3-dimethoxy-3,4-dihydrodibenzo[b,d]furan-1(2H)-one
  参考文献：
  名称：

  Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

  摘要：

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

  DOI：

  10.1021/jo500210k
• 作为产物：
  描述：

  (3aS,4S,5R,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-4-ol 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.5h， 生成 (1R,2S,5R,6R)-3-bromo-5,6-dimethoxycyclohex-3-ene-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

  摘要：

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

  DOI：

  10.1021/jo500210k

文献信息

• Chemoenzymatic Total Synthesis and Reassignment of the Absolute Configuration of Ribisin C
  作者：Ping Lan、Martin G. Banwell、Jas S. Ward、Anthony C. Willis

  DOI：10.1021/ol403220t

  日期：2014.1.3

  enzymatically derived cis-1,2-dihydrocatechol 5 has been converted, by two related pathways, into compounds 3 and ent-3. As a result, it has been determined that the true structure of the natural product ribisin C is represented by ent-3.

  对映体纯和酶促衍生的顺式-1,2-二氢邻苯二酚5已通过两种相关途径转化为化合物3和ent - 3。结果，已经确定天然产物核糖蛋白C的真实结构由ent - 3表示。