5-chloro-1-iodopent-1-yne | 67826-83-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代乙炔及其衍生物
• 英文名称: 5-chloro-1-iodopent-1-yne
• 英文别名: 1-Pentyne, 5-chloro-1-iodo-
• CAS: 67826-83-9
• 化学式: C₅H₆ClI
• 分子量: 228.46
• InChiKey: ZFLKTKYWXYMWCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  bis(cyclohexanyl)borane 、 5-chloro-1-iodopent-1-yne 生成 [(Z)-5-chloropent-1-enyl]-dicyclohexylborane
  参考文献：
  名称：

  An improved synthesis of cis-alkenylboranes

  摘要：

  DOI：

  10.1016/s0022-328x(00)84865-2
• 作为产物：
  描述：

  5-氯戊炔 在 copper(l) iodide 、 四丁基氯化铵 碘 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到5-chloro-1-iodopent-1-yne
  参考文献：
  名称：

  末端炔烃的铜（I）和相转移催化的碘化

  摘要：

  据报道，一种方便的1-iodoalk-1-ynes合成方法涉及在固-液相转移条件下，铜（I）催化的末端炔烃与分子碘的碘化反应。

  DOI：

  10.1039/c39880000909

文献信息

• Highly (≥98%) Stereo- and Regioselective Trisubstituted Alkene Synthesis of Wide Applicability via 1-Halo-1-alkyne Hydro- boration-Tandem Negishi-Suzuki Coupling or Organoborate Migratory Insertion
  作者：Shiqing Xu、Ching-Tien Lee、Honghua Rao、Ei-ichi Negishi

  DOI：10.1002/adsc.201100420

  日期：2011.11

  synthetic utility of the present methodology has been demonstrated in the highly selective synthesis of side chain (4) of scyphostatin in 28% yield over nine steps in the longest linear sequence from allyl alcohol. Thus, this new tandem protocol has been emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to prepare.

  然后用有机锂或格氏试剂处理以产生具有反向立体构型的三取代烯烃。本方法的合成效用已在从烯丙醇以最长线性序列的九个步骤以 28% 的收率高选择性合成 scyphostatin 的侧链 (4) 中得到证明。因此，这种新的串联方案已成为最广泛适用和高度选择性的三取代烯烃路线，包括那些难以制备的烯烃。
• Synthesis of ethynylidene cyclopentanes by a cyclisation catalyzed by the simultaneous presence of palladium (0) and copper (I)
  作者：Didier Bouyssi、Geneviève Balme、Jacques Gore

  DOI：10.1016/0040-4039(91)80215-r

  日期：1991.11

  Ethynylidene cyclopentanes can be formed in 35–71% yield from the reaction of the enolates of compounds such as δ-acetylenic malonates with 1-halogeno-1-alkynes. This reaction requires catalysis by both palladium (0) and copper (I) species.

  乙炔基丙二酸酯等化合物的烯醇化物与1-卤代-1-炔烃的反应可形成亚乙基环戊烷，产率为35-71％。该反应需要钯（0）和铜（I）物种的催化。
• Cascade annulations of aryldiazonium salts, nitriles and halo-alkynes leading to 3-haloquinolines
  作者：Mani Ramanathan、Shiuh-Tzung Liu

  DOI：10.1016/j.tet.2017.05.085

  日期：2017.7

  A regiospecific access to 3-haloquinolines has been developed via a three-component annulation of aryldiazonium salts, nitriles and haloalkynes. This reaction proceeds through an initial formation of reactive nitrilium ion and further cascade annulation with haloalkynes. This method provides a straightforward access to a diverse array of functionalized quinolones (28 examples) under mild conditions

  通过芳基重氮盐，腈和卤代炔烃的三组分环化，已经开发出了对3-卤代喹啉的区域专一性途径。该反应通过反应性腈离子的初步形成并进一步与卤代炔烃级联进行。该方法可在温和条件下直接访问各种功能化的喹诺酮类药物（28个实例），并具有广泛的官能团耐受性。说明了该方法在克规模反应和匹伐他汀正式合成中的应用。
• Iodination of organotrifluoroborates: synthesis of vinyl and alkynyl iodides
  作者：George W. Kabalka、Arjun Reddy Mereddy

  DOI：10.1016/j.tetlet.2003.12.050

  日期：2004.2

  Vinyl- and alkynyltrifluoroborates are rapidly converted to vinyl and alkynyl iodides under mild conditions using sodium iodide in the presence of chloramine-T. The reaction is stereospecific and proceeds in excellent yield.

  在氯胺-T存在下，使用碘化钠在温和条件下将乙烯基和炔基三氟硼酸酯快速转化为乙烯基碘和炔基碘。该反应是立体特异性的，并以优异的产率进行。
• An Alkynyliodide Cycloaddition Strategy for the Construction of Iodoisoxazoles
  作者：James A. Crossley、Duncan L. Browne

  DOI：10.1021/jo1011174

  日期：2010.8.6

  The thermally promoted cycloaddition between alkynyliodides and nitrite oxides is reported. The process offers excellent regioselectivity and a broad scope with respect to both the iodoalkynes and chloro-oximes. Further functionalization of the highly decorated iodoisoxazole motifs can be achieved via Suzuki cross-coupling.