(Z)-3-Iodo-2-nonen-1-ol | 148801-93-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-3-Iodo-2-nonen-1-ol
• CAS: 148801-93-8
• 化学式: C₉H₁₇IO
• 分子量: 268.138
• InChiKey: YFOBHHJCHVRKFS-CLFYSBASSA-N

物化性质

• 沸点：
  281.3±23.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-Iodo-2-nonen-1-ol 在 四溴化碳 、 叔丁基锂 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 4.0h， 生成 二氢茉莉酮
  参考文献：
  名称：

  通过硫代链烯基羧酰胺的环酰化反应合成环戊烯酮和环己烯酮

  摘要：

  1-碘-3-溴丙烯衍生物（1）与N，N-二烷基羧酰胺的烯醇锂反应，然后用两个当量的t- BuLi处理烯丙基化产物（2）干净地提供了高收率的环戊烯酮， 6-碘-5-己酰胺的环酰化反应提供了环己酮。

  DOI：

  10.1016/s0040-4039(00)84098-8

文献信息

• Ruthenium-Catalyzed Aromatization of Enediynes via Highly Regioselective Nucleophilic Additions on a π-Alkyne Functionality. A Useful Method for the Synthesis of Functionalized Benzene Derivatives
  作者：Arjan Odedra、Chang-Jung Wu、Taduri Bhanu Pratap、Chun-Wei Huang、Ying-Fen Ran、Rai-Shung Liu

  DOI：10.1021/ja043047j

  日期：2005.3.1

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 degrees C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1' alkyne carbon of enediynes

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) 催化剂在合适的条件下（100 摄氏度，12-24 小时）实现了水、醇、苯胺、乙酰丙酮、吡咯和丙二酸二甲酯与未官能化的烯二炔的亲核加成和以良好的收率得到官能化苯产物。在这种新颖的环化中，亲核试剂非常区域选择性地攻击烯二炔的内部 C1' 炔烃碳，得到苯衍生物作为单一区域异构体。使用甲氧基取代基的实验排除了萘基阳离子作为反应中间体参与（邻乙炔基苯基）炔烃环化的可能。氘标记实验表明催化活性物质是钌-π-炔烃而不是钌-亚乙烯基物质。o-(2' -碘乙炔基）苯基炔烃与醇。我们在一系列实验的基础上提出了这种亲核芳构化的亲核加成/插入机制。
• Highly stereoselective and general synthesis of (z)-3-methyl-2-alken-1-ols via palladium-catalyzed cross coupling of (z)-3-iodo-2-buten-1-ol with organozincs and other organometals
  作者：Ei-ichi Negishi、Mehmet Ay、Yuri V. Gulevich、Yumiki Noda

  DOI：10.1016/s0040-4039(00)60312-x

  日期：1993.2

  The reaction of Zn-protected (Z)-3-iodo-2-buten-1-ol with organozincs in the presence of 1-5 mol % of a Pd complex, e.g., Pd(PPh3)4 or Cl2Pd(pPh3)2 and n-BuLi (2 equiv), in DMF provides a highly stereoselective (greater-than-or-equal-to 96%), general, and high-yielding procedure for preparing (Z)-3-methyl-2-alken-1-ols, while the use of organometals containing B and Sn along with a Pd catalyst or organocoppers alone gives the desired products in moderate to good yields.
• Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides
  作者：Lin Ming-Yuan、Reniguntala J. Madhushaw、Rai-Shung Liu

  DOI：10.1021/jo048983w

  日期：2004.10.1

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.