(Z)-1-chloro-2-decen | 135457-18-0

• 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: (Z)-1-chloro-2-decen
• 英文别名: (Z)-1-chlorodec-2-ene；(2Z)-1-Chloro-2-decene
• CAS: 135457-18-0
• 化学式: C₁₀H₁₉Cl
• 分子量: 174.714
• InChiKey: BFKFRIMTTLTFAY-HJWRWDBZSA-N

物化性质

• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-1-chloro-2-decen 在 Oxone 、 18-冠醚-6 、 Streptomyces sp. FCC₀₀₈ cells 、 Tris buffer 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 172.0h， 生成 (2R,3R)-1,2-epoxy-3-decanol
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w
• 作为产物：
  描述：

  2-癸炔-1-醇 在 Lindlar's catalyst 喹啉 、 四氯化碳 、 氢氧化钾 、 氢气 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 (Z)-1-chloro-2-decen
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w

文献信息

• Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents
  作者：Akira Yanagisawa、Yasuhiro Yamada、Hisashi Yamamoto

  DOI：10.1055/s-1997-1530

  日期：1997.9

  An increase of α-regioselectivity was observed in the reaction of allylic barium reagents with aldehydes employing crown ether as an additive. For example, an α/γ regioselectivity was improved to 98/2 from 92/8, when an equimolar amount of 18-crown-6 was added to geranylbarium reagent in THF at -78 °C prior to the reaction with benzaldehyde.

  在含冠醚添加剂的反应中，观察到烯丙基钡试剂与醛的反应中α位选择性增加。例如，当在-78°C下将等摩尔量的18-冠-6加入到在THF中的香叶基钡试剂中，并与苯甲醛反应前，α/γ位选择性从92/8提高到98/2。
• α-Selective Allylation of Azo Compounds Using Allylic Barium Reagents
  作者：Akira Yanagisawa、Takuya Jitsukawa、Kazuhiro Yoshida

  DOI：10.1055/s-0032-1318306

  日期：——

  The addition of allylic barium reagents to azo compounds was achieved with high α-regioselectivity. The double-bond geometry of allylic barium reagents was retained throughout the reaction at –78 °C and E- or Z-enriched allylic hydrazines were selectively obtained from the corresponding allylic barium reagents. An allylic hydrazine was efficiently converted into an allylic amine by reductive N–N bond

  以高α-区域选择性将烯丙基钡试剂添加到偶氮化合物中。烯丙基钡试剂的双键几何结构在 –78 °C 的整个反应过程中保持不变，并且从相应的烯丙基钡试剂中选择性地获得富含 E 或 Z 的烯丙基肼。通过还原性 N-N 键断裂，烯丙基肼被有效地转化为烯丙基胺。
• Regio- and Stereoselective Synthesis of 1,5-Dienes Using Allylic Barium Reagents
  作者：Akira Yanagisawa、Hiroaki Hibino、Shigeki Habaue、Yoshiyuki Hisada、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1246/bcsj.68.1263

  日期：1995.5

  The highly α,α′ selective and stereocontrolled homocoupling reaction of allylic halides was achieved using barium reagent. The double-bond geometry of the starting allylic chloride was completely retained. The α,α′ cross-coupling products were also prepared stereospecifically and regioselectively by this method.

  使用钡试剂实现了烯丙基卤化物的高度α,α'选择性和立体控制的同偶联反应。完全保留了起始烯丙基氯的双键几何结构。α,α'交叉偶联产物也通过该方法立体定向和区域选择性制备。
• A short synthesis of (+) and (−)-falcarinol
  作者：Noel P. McLaughlin、Eibhlín Butler、Paul Evans、Nigel P. Brunton、Anastasios Koidis、Dilip K. Rai

  DOI：10.1016/j.tet.2010.10.049

  日期：2010.12

  A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess

  报道了双炔天然产物falcarinol 1的短而实用的合成。该方法依赖于双-三甲基甲硅烷基丁二炔10的替代功能化。这可以在一锅中实现，但是，更常规地获得了更好的产量。脂肪酶介导的外消旋加合物在有机溶剂中的酶促动力学拆分，得到（+）- 1的对映体过量为97％。在水性条件下用外消旋的3-乙酰氧基福尔卡诺醇11进行的类似过程得到（-）- 1。用Dess-Martin高碘烷氧化1可以得到falcarinone 2。
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).