(Z)-3-chloro-2-but-en-1-ol | 37428-46-9

• 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-chloro-2-but-en-1-ol
• 英文别名: (Z) 3-chloro-but-2-en-1-ol；3-chlorocrotyl alcohol；(Z)-3-chloro-but-2-en-1-ol；3-chloro-but-2t-en-1-ol；(Z)-3-Chlor-but-2-en-1-ol；3-Chlor-but-2t-en-1-ol；3-Chloro-2-buten-1-OL；(Z)-3-chlorobut-2-en-1-ol
• CAS: 37428-46-9
• 化学式: C₄H₇ClO
• 分子量: 106.552
• InChiKey: SRQGZQPUPABHCN-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：

  (Z)-3-chloro-2-but-en-1-ol 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以53%的产率得到(Z)-1,3-二氯-2-丁烯
  参考文献：
  名称：

  Synthesis and Evaluation of Chlorinated Substrate Analogues for Farnesyl Diphosphate Synthase

  摘要：

  Substrate analogues for isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where the C3 methyl groups were replaced by chlorine, were synthesized and evaluated as substrates for avian farnesyl diphosphate synthase (FPPase). The IPP analogue (3-ClIPP) was a cosubstrate when incubated with dimethylallyl diphosphate (DMAPP) or geranyl diphosphate (GPP) to give the corresponding chlorinated analogues of geranyl diphosphate (3-ClGPP) and farnesyl diphosphate (3-ClFPP), respectively. No products were detected in incubations of 3-ClIPP with 3-ClDMAPP. Incubation of IPP with 3-ClDMAPP gave 11-ClFPP as the sole product. Values of K(M)(3-ClIPP) (with DMAPP) and K(M)(3-ClDMAPP) (With IPP) were similar to those for [PP and DMAPP; however, values of K(cat) for both analogues were substantially lower. These results are consistent with a dissociative electrophilic alkylation mechanism where the rate-limiting step changes from heterolytic cleavage of the carbon-oxygen bond in the allylic substrate to alkylation of the double bond of the homoallylic substrate.

  DOI：

  10.1021/jo1024305
• 作为产物：
  描述：

  3-chlorocrotonic acid ethyl ester 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 (Z)-3-chloro-2-but-en-1-ol
  参考文献：
  名称：

  Allylic Chlorides. XXII. The 1,3-Dichloro-2-butenes¹

  摘要：

  DOI：

  10.1021/ja01610a015

文献信息

• 5,6,7-Trinor-4,8-inter-m-phenylene prostaglandin I.sub.2 derivatives
  申请人：Toray Industries, Inc.

  公开号：US04474802A1

  公开（公告）日：1984-10-02

  A compound of the formula ##STR1## wherein R.sup.1 is a pharmaceutically acceptable cation, hydrogen or n-alkyl of 1 to 12 carbon atoms; R.sup.2 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R.sup.3 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R.sup.4 is hydrogen, methyl or ethyl; R.sup.5 is n-alkyl of 1 to 5 carbon atoms; n is an integer of 0 to 4; A is --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH--; and X is --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH--. The compounds are useful in anti-ulcer, hypotensive and platelet aggregation inhibiting compositions.

  式##STR1##的化合物，其中R.sup.1是药用阳离子、氢或1至12个碳原子的n-烷基；R.sup.2是氢、2至10个碳原子的酰基或7至13个碳原子的芳酰基；R.sup.3是氢、2至10个碳原子的酰基或7至13个碳原子的芳酰基；R.sup.4是氢、甲基或乙基；R.sup.5是1至5个碳原子的n-烷基；n是0至4的整数；A是--CH.sub.2 --CH.sub.2 --或反式--CH.dbd.CH--；X是--CH.sub.2 --CH.sub.2 --或反式--CH.dbd.CH--。这些化合物在抗溃疡、降压和抑制血小板聚集的组合物中有用。
• Total Synthesis of Aurantoside G, an<i>N</i>-β-Glycosylated 3-Oligoenoyltetramic Acid from<i>Theonella swinhoei</i>
  作者：Markus Petermichl、Sebastian Loscher、Rainer Schobert

  DOI：10.1002/anie.201604912

  日期：2016.8.16

  The first synthesis of a natural N‐glycosylated 3‐acyltetramic acid is reported. Aurantoside G (1 g), a deep‐red metabolite of the marine sponge Theonella swinhoei, is highly delicate in the pure state. It features a chlorinated dodecapentaenoyl side chain at an l‐asparagine‐derived tetramic acid, the ring nitrogen atom of which is linked to a β‐configured d‐xylose. The side chain was built through

  报道了天然的N-糖基化的3-酰基四氢呋喃酸的首次合成。Aurantoside G（1 g）是海洋海绵Theonella swinhoei的深红色代谢产物，在纯净状态下非常细腻。它在l-天冬酰胺衍生的四酸上具有氯化的十二碳五烯酰基侧链，其环氮原子与β-构型的d相连。木糖。侧链是通过连续的Wittig和HWE反应建立的，用于N-酰化已通过Fukuyama-Mitsunobu反应N-木糖基化的天冬酰胺的氨基。此N-酰化步骤可固定木糖的β-构型，这对于抗真菌活性至关重要，但前提是糖带有庞大的，富含电子的保护基团（如PMB）。在最后一步中，通过完全未保护的前体的基本Lacey-Dieckmann缩合将杂环定量关闭。
• Selective oxidation of primary alcohols with chromium trioxide under solvent free conditions
  作者：Ji-Dong Lou、Zhi-Nan Xu

  DOI：10.1016/s0040-4039(02)01333-3

  日期：2002.8

  Selective oxidation of primary alcohols to the corresponding aldehydes by chromium trioxide under solvent free conditions are described. This new oxidation procedure is simple and affords good yields.

  描述了在无溶剂条件下通过三氧化铬将伯醇选择性氧化为相应的醛。这种新的氧化过程很简单，收率很高。
• Selective solvent-free oxidation of alcohols with potassium dichromate
  作者：Ji-Dong Lou、Zhi-Nan Xu

  DOI：10.1016/s0040-4039(02)02234-7

  日期：2002.12

  Selective oxidation of primary alcohols to the corresponding aldehydes by potassium dichromate at room temperature under solvent-free conditions are described. This new procedure can also oxidise secondary alcohols.

  描述了在室温下在无溶剂条件下通过重铬酸钾将伯醇选择性氧化为相应的醛的方法。这种新方法也可以氧化仲醇。
• Efficient Oxidation of Alcohols with Potassium Permanganate Adsorbed on Aluminum Silicate Reagent
  作者：Lan-Zhou Wang、Ji-Dong Lou、Li-Yun Zhu

  DOI：10.1007/s00706-003-0098-x

  日期：2004.1.1

  A new reagent, potassium permanganate adsorbed on aluminum silicate, suitable for the oxidation of primary and secondary alcohols to the corresponding carbonyl compounds is described.

  描述了一种新的试剂，高锰酸钾吸附在硅酸铝上，适用于将伯醇和仲醇氧化为相应的羰基化合物。

表征谱图