2-methyl-3-butyn-2-ol-4,O-d2 | 118723-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-butyn-2-ol-4,O-d2
• 英文别名: 2-methylbut-3-yn-4-d-2-ol-d；4,O-dideuterio-2-methyl-but-3-yn-2-ol；1-deuterio-3-deuteriooxy-3-methylbut-1-yne
• CAS: 118723-86-7
• 化学式: C₅H₈O
• 分子量: 86.102
• InChiKey: CEBKHWWANWSNTI-UPXKZQJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-butyn-2-ol-4,O-d2 在 lithium aluminium deuteride 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Oxiranylcarbinyl Radicals from Allyloxyl Radical Cyclization:  Characterization and Kinetic Information via ESR Spectroscopy¹

  摘要：

  An ESR spin-trapping technique has been used for the detection of oxiranylcarbinyl radicals as discrete reaction intermediates, formed via cyclization of allyloxyl radicals. The latter were obtained by photolysis of the corresponding nitrites, which were generated directly via an exchange reaction between the appropriate allylic alcohols and tert-butyl nitrite (which also acts as the spin-trap). Experiments have also been conducted with the spin-trap 2,4,6-tribromonitrosobenzene, which has allowed a study to be made of the competition between ring closure and p-scission of a variety of allyloxyl species.

  DOI：

  10.1021/jo9812678
• 作为产物：
  描述：

  2-甲基-3-丁炔-2-醇 在 正丁基锂 、 重水 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以57%的产率得到2-methyl-3-butyn-2-ol-4,O-d2
  参考文献：
  名称：

  在二钌配合物上乙烯基分子与烯基配体的碳-碳键偶联

  摘要：

  二钌μ-丙二烯基配合物[Ru 2 Cp 2 (CO) 2 (NCMe){μ-η 1 :η 2 -CH=C= CMe 2 }]BF 4 , 3-NCMe与一系列烯烃，RCH=CH 2，得到配合物[Ru 2 Cp 2 (CO) 2 {μ-η 3 :η 2 -CH( R )CHC(Me)C( Me )CH 2 }]BF 4 (R ═Ph, 4 ; 4-C 6 H 4 Me, 5 ; Me, 6; n卜, 7 ; 一氧化碳2我, 8 ; 和 H, 9 )，含有不常见的五碳烯基-烯丙基配体。氘代试剂交叉实验，即[Ru 2 Cp 2 (CO) 2 (NCMe){μ-η 1 :η 2 -CD=C= CMe 2 }]BF 4 ( 3b-NCMe )和CD 2 ═CD( C 6 H 5 ) (苯乙烯- d 3 ), 表明形成4-9由烯烃攻击丙二烯基部分的中心碳引发，引发两个不同的 C-H 活化过程。在4、7

  DOI：

  10.1021/acs.organomet.2c00060

文献信息

• Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes
  作者：Juan J. González、Andrés Francesch、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1021/jo9717853

  日期：1998.5.1

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.
• Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis
  作者：Volker Stanjek、Martin Miksch、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)10237-x

  日期：1997.12

  Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer-hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (beta-cleavage). (C) 1997 Elsevier Science Ltd.
• Biosynthesis of Angular Furanocoumarins: Mechanism and Stereochemistry of the Oxidative Dealkylation of Columbianetin to Angelicin inHeracleum mantegazzianum (Apiaceae)
  作者：Volker Stanjek、Wilhelm Boland

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1596::aid-hlca1596>3.0.co;2-f

  日期：1998.9.9

  Deuterium-labelled 5-fluorocolumbianetin 13 was synthesized as a metabolic probe to examine the stereochemical course of the bioconversion of (+)-columbianetin (12) into the angular furocoumarin angelicin (5). In leaves of Heracleum mantegazzianum, oxidative dealkylation of the specifically deuterated fluorocolumbianetin 13 proceeded by syn-elimination of a D-atom, from C(9), and the vicinal 1-hydroxy-1-methylethyl substituent, yielding 5-fluoroangelicin (23). This matches the stereochemical course of the related reaction converting (+)-marmesin (10) into the linear furocoumarin psoralen (1). Key steps in the synthesis of 5-fluorocolumbianetin (13) were the copper-catalysed alkynylation/cyclization of 5-fluoro-8-iedoumbelliferone (15) followed by a transfer hydrogenation, which established the cis-orientation of the D-Atom and the 1-hydroxy-1-methylethyl substituent.