6-chlorohex-4-yn-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chlorohex-4-yn-3-ol
• 英文别名: 6-chloro-4-hexyn-3-ol
• 化学式: C₆H₉ClO
• mdl: MFCD19233138
• 分子量: 132.59
• InChiKey: VLXADHCFPIRRPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chlorohex-4-yn-3-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes

  摘要：

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02126-0
• 作为产物：
  描述：

  3-氯丙炔 、 丙醛 在 正丁基锂 、 水 、 氯化铵 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.33h， 以93%的产率得到6-chlorohex-4-yn-3-ol
  参考文献：
  名称：

  从光学活性的1取代的4-氯-2-丁炔-1-醇的高效CuCN催化合成光学活性的2,3-烯丙醇

  摘要：

  用n- BuLi /（HCHO）n连续处理旋光性末端炔丙醇并进行区域选择性氯化，得到相应的旋光性4-氯-2-丁炔-1-醇。当R 1为甲基或乙基时，合成相应的旋光炔丙醇的另一种方法是由Novozym 435催化的这些外消旋4-氯-2-丁炔-1-醇的动力学拆分。这些旋光的4-氯-2-丁炔-1-醇与相应的格氏试剂的随后反应在5 mol％的CuCN的催化下以良好的收率提供了旋光的仲2,3-烯醇，收率高达> 99 ％ee。

  DOI：

  10.1021/jo900710e

文献信息

• Tungsten-Promoted Intramolecular Alkoxycarbonylation for Synthesis of Complex Oxygenated Molecules
  作者：Chi-Chung Chen、Jang-Shyang Fan、Su-Ju Shieh、Gene-Hsian Lee、Shie-Ming Peng、Sue-Lang Wang、Rai-Shung Liu

  DOI：10.1021/ja9617808

  日期：1996.1.1

  Intramolecular alkoxycarbonylation of tungsten-propargyl compounds proceeds with excellent diastereoselectivities to form eta(3)-delta- and -epsilon-lactones but for gamma-lactones. With OSi(t-Bu)Me(2) substituted for an or-hydroxy group, eta(3)-gamma-lactones are stereoselectively formed with syn stereoselection. An optically active tungsten eta(3)-gamma-lactone is prepared from D-(+)-xylose to illustrate the stereochemical effect of OSi(t-Bu)Me(2). All these eta(3)-gamma-, -delta-, and -epsilon-lactones are converted to allyl anions that react in situ with aldehydes and ketones to produce various beta-(hydroxylalkyl)-alpha-methylene-gamma-lactones with good diastereoselectivity. This reaction is also applied to the synthesis of chiral alpha-methylene butyrolactones. Organic carbonyls add to the pi-allyl groups of eta(3)-gamma- and -delta-lactones opposite the tungsten fragment, whereas additions occur from the metal side for eta(3)-epsilon-lactones. The stereochemical courses of these reactions are discussed in detail. These two tungsten-promoted reactions efficiently effect stereoselective transformation of chloroalkynols to complex alpha-methylene-gamma-lactones, which are useful materials for syntheses of trisubstituted 1,3-, 1,4-, and 1-5-diols.
• Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes
  作者：Sentaro Okamoto、Hiroyoshi Sato、Fumie Sato

  DOI：10.1016/s0040-4039(96)02126-0

  日期：1996.12

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.
• An Efficient CuCN-Catalyzed Synthesis of Optically Active 2,3-Allenols from Optically Active 1-Substituted 4-Chloro-2-butyn-1-ols
  作者：Jing Li、Wangqing Kong、Chunling Fu、Shengming Ma

  DOI：10.1021/jo900710e

  日期：2009.7.17

  The sequential treatment of optically active terminal propargylic alcohols with n-BuLi/(HCHO)n and regioselective chlorination afforded the corresponding optically active 4-chloro-2-butyn-1-ols. With R1 being a methyl or an ethyl group, an alternative for the synthesis of the corresponding optically active propargylic alcohols is the Novozym 435-catalyzed kinetic resolution of these racemic 4-chloro-2-butyn-1-ols

  用n- BuLi /（HCHO）n连续处理旋光性末端炔丙醇并进行区域选择性氯化，得到相应的旋光性4-氯-2-丁炔-1-醇。当R 1为甲基或乙基时，合成相应的旋光炔丙醇的另一种方法是由Novozym 435催化的这些外消旋4-氯-2-丁炔-1-醇的动力学拆分。这些旋光的4-氯-2-丁炔-1-醇与相应的格氏试剂的随后反应在5 mol％的CuCN的催化下以良好的收率提供了旋光的仲2,3-烯醇，收率高达> 99 ％ee。