chloro-1 butyne-1 ol-4 | 98352-48-8

• 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: chloro-1 butyne-1 ol-4
• 英文别名: 4-chlorobut-3-yn-1-ol；4-Chlor-but-3-in-1-ol
• CAS: 98352-48-8
• 化学式: C₄H₅ClO
• 分子量: 104.536
• InChiKey: XLUBCXUNKUAHMI-UHFFFAOYSA-N

物化性质

• 沸点：
  67 °C(Press: 18 Torr)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  chloro-1 butyne-1 ol-4 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 以3.31 g的产率得到(E)-4-chlorobut-3-en-1-ol
  参考文献：
  名称：

  Isolation and Total Synthesis of Beru’amide, an Antitrypanosomal Polyketide from a Marine Cyanobacterium Okeania sp.

  摘要：

  DOI：

  10.1021/acs.orglett.2c02013
• 作为产物：
  描述：

  4-(叔丁基二甲基硅杂氧基)-1-丁炔 在 正丁基锂 、 对甲苯磺酰氯 、 硫酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 21.0h， 生成 chloro-1 butyne-1 ol-4
  参考文献：
  名称：

  de Mayo反应的炔烃类似物的开发：中型碳环化合物和环庚[b]吲哚的合成

  摘要：

  嵌入的中型碳环化合物和环庚[b]吲哚经常作为天然产物和生物活性化合物中的支架元素出现。本文描述了对这些支架的概念上新颖的光化学触发的级联过程。级联扩环过程的关键是de Mayo反应的前所未有的分子内炔烃类似物。

  DOI：

  10.1002/anie.201808578

文献信息

• Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio‐ and Stereoselective Synthesis of Trifluoromethoxylated Alkenes
  作者：Zhichao Lu、Tatsuya Kumon、Gerald B. Hammond、Teruo Umemoto

  DOI：10.1002/anie.202104975

  日期：2021.7.12

  The trifluoromethoxy group has elicited much interest among drug and agrochemical discovery teams because of its unique properties. We developed trifluoromethyl nonafluorobutanesulfonate (nonaflate), TFNf, an easy-to-handle, bench-stable, reactive, and scalable trifluoromethoxylating reagent. TFNf is easily and safely prepared in a simple process in large scale and the nonaflyl part of TFNf can easily

  三氟甲氧基因其独特的性质而引起了药物和农用化学品发现团队的极大兴趣。我们开发了九氟丁烷磺酸三氟甲酯 (nonaflate) TFNf，这是一种易于操作、实验室稳定、反应性且可扩展的三氟甲氧基化试剂。 TFNf可以通过简单的工艺轻松、安全地大规模制备，并且TFNf的九氟部分在使用后可以很容易地以九氟氟化物的形式回收并循环利用。通过对卤代炔、炔基酯和炔基砜等炔衍生物进行高区域和立体选择性氢（卤）三氟甲氧基化，各种三氟甲氧基化烯烃的合成展现了 TFNf 的合成潜力。三氟甲磺酸烷基酯/溴化物和伯/仲醇的高产率且顺利的亲核三氟甲氧基化进一步凸显了 TFNf 的合成优点。
• Julia; Surzur, Bulletin de la Societe Chimique de France, 1956, p. 1626,1629
  作者：Julia、Surzur

  DOI：——

  日期：——
• A model of the thermal processing of particles in solar nebula shocks: Application to the cooling rates of chondrules
  作者：S. J. DESCH、H. C. CONNOLLY

  DOI：10.1111/j.1945-5100.2002.tb01104.x

  日期：2002.2

  Abstract— We present a model for the thermal processing of particles in shock waves typical of the solar nebula. This shock model improves on existing models in that the dissociation and recombination of H2 and the evaporation of particles are accounted for in their effects on the mass, momentum and energy fluxes. Also, besides thermal exchange with the gas and gas‐drag heating, particles can be heated by absorbing the thermal radiation emitted by other particles. The flow of radiation is calculated using the equations of radiative transfer in a slab geometry. We compute the thermal histories of particles as they encounter and pass through the shock.We apply this shock model to the melting and cooling of chondrules in the solar nebula. We constrain the combinations of shock speed and gas density needed for chondrules to reach melting temperatures, and show that these are consistent with shock waves generated by gravitational instabilities in the protoplanetary disk. After their melting, cooling rates of chondrules in the range 10–1000 K h−1 are naturally reproduced by the shock model. Chondrules are kept warm by the reservoir of hot shocked gas, which cools only as fast as the dust grains and chondrules themselves can radiate away the gas's energy. We predict a positive correlation between the concentration of chondrules in a region and the cooling rates of chondrules in that region. This correlation is supported by the unusually high frequency of (rapidly cooled) barred chondrules among compound chondrules, which must have collided preferentially in regions of high chondrule density. We discuss these and other compelling consistencies between the meteoritic record and the shock wave model of chondrule formation.
• Development of an Alkyne Analogue of the de Mayo Reaction: Synthesis of Medium‐Sized Carbacycles and Cyclohepta[ <i>b</i> ]indoles
  作者：David Tymann、Dina Christina Tymann、Ulf Bednarzick、Ljuba Iovkova‐Berends、Julia Rehbein、Martin Hiersemann

  DOI：10.1002/anie.201808578

  日期：2018.11.19

  herein is a conceptionally novel photochemically triggered cascade process to these scaffolds. Key to the cascading ring‐expansion process is an unprecedented intramolecular alkyne analogue of the de Mayo reaction.

  嵌入的中型碳环化合物和环庚[b]吲哚经常作为天然产物和生物活性化合物中的支架元素出现。本文描述了对这些支架的概念上新颖的光化学触发的级联过程。级联扩环过程的关键是de Mayo反应的前所未有的分子内炔烃类似物。
• Isolation and Total Synthesis of Beru’amide, an Antitrypanosomal Polyketide from a Marine Cyanobacterium <i>Okeania</i> sp.
  作者：Raimu Taguchi、Arihiro Iwasaki、Akira Ebihara、Ghulam Jeelani、Tomoyoshi Nozaki、Kiyotake Suenaga

  DOI：10.1021/acs.orglett.2c02013

  日期：2022.7.1