2-Brom-1-methyl-cyclopropylmethanol | 343267-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Brom-1-methyl-cyclopropylmethanol
• 英文别名: (1-Methyl-3-bromocyclopropyl)methanol；(2-bromo-1-methylcyclopropyl)methanol
• CAS: 343267-94-7
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: XPVIADXMRUCZDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-Brom-1-methyl-cyclopropylmethanol 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-methoxymethyl-3-methylcyclopropene
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k
• 作为产物：
  描述：

  methyl 2-bromo-1-methylcyclopropanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以89%的产率得到2-Brom-1-methyl-cyclopropylmethanol
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k

文献信息

• Highly Diastereo- and Regioselective Transition Metal-Catalyzed Additions of Metal Hydrides and Bimetallic Species to Cyclopropenes:  Easy Access to Multisubstituted Cyclopropanes
  作者：Alexander Trofimov、Marina Rubina、Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/jo701855c

  日期：2007.11.1

  The first highly efficient, diastereo- and regioselective transition metal-catalyzed addition of metal hydrides (stannanes, silanes, and germanes) and bimetallic species (ditins and silyltins) to cyclopropenes has been developed. It was shown that the addition across the double bond of cyclopropenes is generally controlled by steric factors and proceeds from the least hindered face. This methodology

  已经开发出第一种高效的，非对映的和区域选择性的过渡金属催化的金属氢化物（锡烷，硅烷和锗烷）和双金属物质（二锡和甲硅烷基锡）添加到环丙烯中。结果表明，环丙烯双键的加成通常受空间因素控制，并且从受阻最小的面开始。这种方法论代表了一种针对各种高度取代的立体定义的环丙基金属的有力且原子经济的方法，而其他方法则无法提供有用的构建基块。
• Palladium-Catalyzed Living/Controlled Vinyl Addition Polymerization of Cyclopropenes
  作者：Zepeng Zhang、Yunpeng Gao、Shufeng Chen、Jianbo Wang

  DOI：10.1021/jacs.1c09071

  日期：2021.10.27

  and ring-opening metathesis polymerization (ROMP), their vinyl addition polymerization has been sporadically explored, and the corresponding living/controlled polymerization remains a formidable challenge. The major obstacle is the intrinsic instability of the intermediate and the kinetic barrier for propagation. Herein a living/controlled vinyl addition polymerization of 3-methyl-3-carboxymethyl CPEs

  尽管环丙烯 (CPE) 在有机合成和开环复分解聚合 (ROMP) 中具有多种用途，但它们的乙烯基加成聚合已被零星探索，相应的活性/受控聚合仍然是一项艰巨的挑战。主要障碍是中间体的内在不稳定性和传播的动力学障碍。本文展示了由亚磺酰胺双膦配体连接的[Pd(π-allyl)Cl] 2催化的 3-甲基-3-羧甲基 CPE 的活性/受控乙烯基加成聚合。发现在聚合过程中数均分子量 ( M n ) 与转化率的关系图是线性的，分子量分散度 ( M w /M n ) 保持狭窄。Mn值随着单体与催化剂的初始进料比的增加而线性增加。此外，通过顺序单体添加控制嵌段共聚是成功的。所有这些点都证实了这种聚合的活性。催化剂配体和环丙烯部分中的侧羰基的协同配位作用对于以活性/可控方式实现高效聚合起着关键作用。
• Directed Catalytic Asymmetric Olefin Metathesis. Selectivity Control by Enoate and Ynoate Groups in Ru-Catalyzed Asymmetric Ring-Opening/Cross-Metathesis
  作者：Russell E. Giudici、Amir H. Hoveyda

  DOI：10.1021/ja070187v

  日期：2007.4.1

  concept in catalytic asymmetric olefin metathesis is introduced: a nonreacting enoate or ynoate group can be used to alter and significantly enhance the enantioselectivity. Catalytic asymmetric ring-opening/cross-metathesis (AROM/CM) processes proceed in ≤30% ee with non-styrenyl cross partners. However, with olefin partners bearing an enoate or ynoate group (1,6-diene or 1,6-enyne), catalytic AROM/CM

  引入了催化不对称烯烃复分解的新概念：非反应性烯酸酯或炔酸酯基团可用于改变和显着提高对映选择性。催化不对称开环/交叉复分解 (AROM/CM) 过程在≤30% ee 的情况下与非苯乙烯基交叉伙伴进行。然而，由于烯烃伙伴带有烯酸酯或炔酸酯基团（1,6-二烯或 1,6-烯炔），催化 AROM/CM 可提供高达 98% ee 的所需产物，与与苯乙烯反应的对映选择性相反或脂肪族交叉伙伴。这种新方法首次将有效金属催化的 AROM/CM 的范围扩展到非苯乙烯基烯烃和环丙烯的反应，这是一组多样化且易于获得的底物，
• SYDNES L. K.; SKATTEBOL L., ACTA CHEM. SCAND., 1978, B 32, NO 9, 632-638
  作者：SYDNES L. K.、 SKATTEBOL L.

  DOI：——

  日期：——
• LATYPOVA, M. M.;KATERINICH, L. V.;BARANOVA, I. N.;PLEMENKOV, V. V.;BOLESO+, ZH. ORGAN. XIMII, 1982, 18, N 12, 2552-2558
  作者：LATYPOVA, M. M.、KATERINICH, L. V.、BARANOVA, I. N.、PLEMENKOV, V. V.、BOLESO+

  DOI：——

  日期：——