(Z,4S,5R)-5-chloro-4-hydroxydec-7-en-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z,4S,5R)-5-chloro-4-hydroxydec-7-en-2-one
• 化学式: C₁₀H₁₇ClO₂
• 分子量: 204.697
• InChiKey: PAJINEDHQODDMJ-OOMSKYPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,4S,5R)-5-chloro-4-hydroxydec-7-en-2-one 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以85%的产率得到(Z,2R,4S,5R)-5-chlorodec-7-ene-2,4-diol
  参考文献：
  名称：

  A General Strategy for the Stereocontrolled Preparation of Diverse 8- and 9-Membered Laurencia-Type Bromoethers

  摘要：

  A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.

  DOI：

  10.1021/ja2069449
• 作为产物：
  描述：

  顺式-4-庚烯醛 在 N-氯代丁二酰亚胺 、 L-脯氨酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (Z,4S,5R)-5-chloro-4-hydroxydec-7-en-2-one
  参考文献：
  名称：

  A General Strategy for the Stereocontrolled Preparation of Diverse 8- and 9-Membered Laurencia-Type Bromoethers

  摘要：

  A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.

  DOI：

  10.1021/ja2069449

文献信息

• UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY
  申请人：Snyder Scott Alan

  公开号：US20140243404A1

  公开（公告）日：2014-08-28

  This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is:

  本披露涉及有用于多烯环化、烯酸和烯基烷醚环化以及芳香族化合物卤代的卤化物化合物。披露了这种卤化物化合物的合成、使用这种卤化物化合物制备的化合物以及使用卤化物化合物合成天然化合物，包括蒎烯。本披露的代表性卤化物化合物为：
• A General Strategy for the Stereocontrolled Preparation of Diverse 8- and 9-Membered <i>Laurencia</i>-Type Bromoethers
  作者：Scott A. Snyder、Daniel S. Treitler、Alexandria P. Brucks、Wesley Sattler

  DOI：10.1021/ja2069449

  日期：2011.10.12

  A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.