(R)-2-ethyl-4-penten-1-ol | 89790-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-ethyl-4-penten-1-ol
• 英文别名: (2R)-2-ethylpent-4-en-1-ol
• CAS: 89790-39-6
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: HAAXJIXTDRFJBI-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (R)-2-ethyl-4-penten-1-ol 在 palladium on activated charcoal chromium(VI) oxide 、 sodium hydroxide 、 正丁基锂 、 高氯酸 、 dimethyl sulfide borane 、 硫酸 、 氢气 、 双氧水 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 91.25h， 生成 (R)-2-ethyl-1-hydroxy-7,9,9-trimethoxynon-6-en-5-one
  参考文献：
  名称：

  A synthesis of (-)-talaromycin A

  摘要：

  DOI：

  10.1021/jo00266a030
• 作为产物：
  描述：

  (4R,5S)-3-[(2R)-2-ethylpent-4-enoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以56%的产率得到(R)-2-ethyl-4-penten-1-ol
  参考文献：
  名称：

  Syntheses of 20'-deoxyvinblastine, 20'-deoxyleurosidine, 20'-deoxyvincovaline, 20'-epi-20'-deoxyvincovaline, and 20'-deoxyvincristine and its 20'-epimer through racemic and enantioselectively generated intermediates. New syntheses of D/E-cis- and trans-.PSI.-vincadifformines and D/E-cis- and -trans-20-epi-.PSI.-vincadifformines

  摘要：

  DOI：

  10.1021/jo00275a029

文献信息

• Synthesis of (-)-talaromycins a and b
  作者：Kenji Mori、Masaya Ikunaka

  DOI：10.1016/s0040-4020(01)89929-4

  日期：1987.1

  Highly enantiomerically pure (-)-talaromycins A and B [ (3,4,6,9)- and (3,4,6,9)-9-ethyl-4-hydroxy-3-hydroxymethyl-1,7-dioxaspiro [5.5]undecane] were synthesized starting from chiral building blocks of microbial origin.

  高度对映体纯（ - ） - talaromycins甲乙[（3 ，4 ，6 ，9 ） -和（3 ，4 ，6 ，9 ）-9-乙基-4-羟基-3-羟甲基-1,7-二氧杂螺[5.5]十一烷]是从微生物来源的手性构件开始合成的。
• Assignment of stereochemistry in the oligomycin/rutamycin/cytovaricin family of antibiotics. Asymmetric synthesis of the rutamycin spiroketal synthon
  作者：David A. Evans、Dale L. Rieger、Todd K. Jones、Stephen W. Kaldor

  DOI：10.1021/jo00313a011

  日期：1990.12

  The absolute stereochemistry of the rutamycin antibiotics 2a,b has been established through asymmetric synthesis of the known degradation product 4. One of the key steps in the assemblage process involves acylation of the metalated hydrazone 6 with the N-methoxy-N-methyl amide 5. Both of these enantiomerically pure intermediates have been prepared in good overall yield and high diastereoselectivity (de > 94%). All absolute stereochemical relationships were established through alkylation and aldol bond constructions using N-acyloxazolidinone chiral auxiliaries. Subjection of 17 to acid hydrolysis/deprotection resulted in loss of protecting groups and subsequent spiroketalization to 19 (80%). Silylation of the secondary alcohol in 19 was followed by a samarium-catalyzed Meerwein-Ponndorf-Verley reduction to provide the equatorial alcohol 20 in excellent yield and stereoselectivity (de = 97%). Control experiments indicate that this surprisingly stereoselective reaction operates under kinetic control and that the observed stereochemical outcome may be the result of coordination of the reactive reducing agent to the axial spiroketal oxygen. Conversion of 20 to triol 4 afforded material that is identical with the rutamycin degradation product in all respects. These results establish that the absolute stereochemistry of the rutamycins is as shown (2a,b).
• An enantioselective total synthesis of (-)-talaromycins A and B
  作者：Amos B. Smith、Andrew S. Thompson

  DOI：10.1021/jo00182a041

  日期：1984.4
• High-Yielding Enantioselective Synthesis of the Macrolactam Aglycon of Sch 38516 from Two Units of (2R)-2-Ethyl-4-penten-1-ol
  作者：Manuel Martín、Gemma Mas、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1002/(sici)1521-3773(19991018)38:20<3086::aid-anie3086>3.0.co;2-d

  日期：1999.10.18
• CRIMMINS, MICHAEL T.;OMAHONY, ROSEMARY, J. ORG. CHEM., 54,(1989) N, C. 1157-1161
  作者：CRIMMINS, MICHAEL T.、OMAHONY, ROSEMARY

  DOI：——

  日期：——