(6Z)-2-chloro-6-nonenal | 1334227-44-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: (6Z)-2-chloro-6-nonenal
• 英文别名: (Z)-2-chloronon-6-enal
• CAS: 1334227-44-9
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: ZZBSALQBWZJRCF-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6Z)-2-chloro-6-nonenal 在 sodium tetrahydroborate 、 正丁基锂 、 bromodiethylsulfonium bromopentachloroantimonate 、 水 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 正己烷 为溶剂， 反应 7.0h， 生成
  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：

  1-己醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 在 N-氯代丁二酰亚胺 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 L-脯氨酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (6Z)-2-chloro-6-nonenal
  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

• Trichloromethanesulfonyl Chloride: A Chlorinating Reagent for Aldehydes
  作者：Ciril Jimeno、Lidong Cao、Philippe Renaud

  DOI：10.1021/acs.joc.5b02543

  日期：2016.2.5

  commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste

  已经发现三氯甲磺酰氯（CCl 3 SO 2 Cl），一种可商购的试剂，在非常温和的反应条件下，在醛的α-氯化反应中，包括催化的不对称形式，都能有效地进行醛的氯化反应。在我们的反应条件下，该化合物的性能优于用于有机合成的典型氯化试剂，有助于产品的后处理和纯化，并最大程度地减少了有毒的氯化有机废物的形成。
• 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：
• [EN] UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY<br/>[FR] CYCLISATIONS PARTICULIÈRES INDUITES PAR HALOGÈNE, RÉACTIFS POUR CELLES-CI ET COMPOSÉS AINSI PRODUITS
  申请人：UNIV COLUMBIA

  公开号：WO2012037069A2

  公开（公告）日：2012-03-22

  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: Formula (I).
• 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.