3-Iodo-2-propen-1-ol | 71065-45-7

• 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: 3-Iodo-2-propen-1-ol
• 英文别名: 3-Iod-2-propen-1-ol；3-iodo-prop-2-en-1-ol；Jodallylalkohol；3-iodoprop-2-en-1-ol
• CAS: 71065-45-7
• 化学式: C₃H₅IO
• 分子量: 183.977
• InChiKey: QPQXCZGFJJMKHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-Iodo-2-propen-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-溴-1-碘丙烯
  参考文献：
  名称：

  A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization

  摘要：

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.

  DOI：

  10.1021/jo00011a008
• 作为产物：
  描述：

  3-iodoacrylic acid methyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-Iodo-2-propen-1-ol
  参考文献：
  名称：

  vic-三羰基化合物的不对称烯丙基硼化：（+）-阿瓦那霉素的全合成

  摘要：

  到核心：（+）的一种有效的全合成-达到起始用的不对称allylboration awajanomycin VIC三羰化合物（参见方案; TES =三乙基甲硅烷）。立体选择性烯烃二羟基化，随后非对映体酯基团的分化和随后的内酰胺化得到双环核心结构。

  DOI：

  10.1002/anie.201103679

文献信息

• First stereoselective total synthesis of pectinolide H
  作者：D. Ramesh、V. Shekhar、D. Chantibabu、S. Rajaram、U. Ramulu、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2011.12.122

  日期：2012.3

  The stereoselective total synthesis of bio-active pectinolide H (1) is described. Midland’s asymmetric reduction, Sharpless dihydroxylation reactions are involved in generating the stereogenic centers at C-4′, C-5 and C-1′. Other key steps in the synthesis are Sonogashira cross coupling, Z-selective Still–Gennari olefination, one-pot acetonide deprotection–lactonization, and Lindlar’s reaction. This

  描述了生物活性果胶内酯H（1）的立体选择性全合成。Midland的不对称还原，Sharpless二羟基化反应参与生成C-4'，C-5和C-1'的立体中心。合成过程中的其他关键步骤是Sonogashira交叉偶联，Z选择性Still–Gennari烯烃化，一锅丙酮化物脱保护–内酯化和Lindlar反应。这为γ-内酯的合成提供了独特的策略。
• 一种氘代异喹啉-氨基嘧啶类化合物、药物组合物和用途
  申请人：药康众拓（北京）医药科技有限公司

  公开号：CN116903593A

  公开（公告）日：2023-10-20

  本发明公开了式I所示化合物、或其药学上可接受的盐、异构体、代谢产物、前药、溶剂合物或水合物，药物组合物和用途。本发明提供的式I所示的氘代异喹啉‑氨基嘧啶类化合物对EGFR突变体具有很好的抑制活性，对癌症特别是非小细胞肺癌具有良好的治疗作用。#imgabs0#
• Cobalt-Catalyzed Enantioselective Cross-Electrophile Couplings: Stereoselective Syntheses of 5–7-Membered Azacycles
  作者：Zhaoming Ma、Wenqiang Xu、Yun-Dong Wu、Jianrong Steve Zhou

  DOI：10.1021/jacs.3c02829

  日期：2023.8.2

  chiral pyrox ligands catalyzed enantioselective reductive couplings of nonconjugated iododienes with aryl iodides or alkenyl bromides. The reaction enabled stereoselective syntheses of 5–7-membered azacycles carrying quaternary stereocenters. Mechanistically, cross-electrophile selectivity originated from selective coupling of alkylcobalt(I) complexes generated after cyclization with aryl iodides.

  手性辉石配体的钴配合物催化非共轭碘二烯与芳基碘或烯基溴的对映选择性还原偶联。该反应能够立体选择性合成带有四元立构中心的 5-7 元氮杂环。从机理上讲，交叉亲电子选择性源于与芳基碘化物环化后生成的烷基钴（I）络合物的选择性偶联。
• Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait
  作者：Francis Beaumier、Marianne Dupuis、Claude Spino、Claude Y. Legault

  DOI：10.1021/ja211927b

  日期：2012.4.4

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.
• Synthesis, radiosynthesis and first in vitro evaluation of novel PET-tracers for the dopamine transporter: [11C]IPCIT and [18F]FE@IPCIT
  作者：Christina Rami-Mark、Birgit Bornatowicz、Cornel Fink、Paul Otter、Johanna Ungersboeck、Chrysoula Vraka、Daniela Haeusler、Lukas Nics、Helmut Spreitzer、Marcus Hacker、Markus Mitterhauser、Wolfgang Wadsak

  DOI：10.1016/j.bmc.2013.10.046

  日期：2013.12

  Introduction: Present data indicate that merging beneficial structural elements from previously published DAT-ligands highest DAT affinity, selectivity and a suitable metabolic profile should be achieved. This combination led to the development of IPCIT and [e-mail]: Precursor synthesis was done starting from cocaine in a six step reaction. O-[C-11]-methylation was established using [C-11]methyl iodide, optimized and subsequently automated. Small scale F-18-fluroroethylation as well as optimization of reaction parameters and automation were performed. Affinity and selectivity of the candidate substances were tested in standard binding experiments on human membranes. Metabolic stability and blood-brain-barrier (BBB) penetration were determined.Results: Precursor compound, IPCITacid, and reference compounds, IPCIT and FE@IPCIT, were obtained in 4.9%, 12.7% and 4.1% yield, respectively. Automated radiosynthesis of [C-11]IPCIT yielded 1.9 +/- 0.7 GBq (12.5 +/- 4%, corrected for decay). Optimum parameters for F-18-fluoroethylation were 110 degrees C for 15 min under TBAH catalysis, yielding 67 +/- 16% radiochemical incorporation. Affinity was determined as 1.7 +/- 0.6 nM for IPCIT, 1.3 +/- 0.2 nM for FE@IPCIT and 37 +/- 13 nM for the precursor molecule, IPCIT-acid. Results from in vitro and in silico evaluations revealed high stability but also high lipophilicity.Conclusion: Present data indicate high affinity and stability of both IPCIT and FE@IPCIT. Radiolabelling, optimization of reaction parameters and automation succeeded. On the other hand, data concerning BBB-penetration are not promising. (C) 2013 Elsevier Ltd. All rights reserved.