2,2-dimethyl-1-ferrocenyl-but-3-en-1-ol | 396718-47-1

• 英文名称: 2,2-dimethyl-1-ferrocenyl-but-3-en-1-ol
• CAS: 396718-47-1
• 化学式: C₁₆H₂₀FeO
• 分子量: 284.181
• InChiKey: MHWUKEUDSTUEDQ-YQFADDPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  二茂铁甲醛 、 天然橡胶 在 锰 、 2-(2-(diphenylphosphaneyl)phenyl)-4-isopropyl-4,5-dihydrooxazole 、 cobalt(II) bromide 、 2-萘甲酸 作用下， 以 丙酮 、 叔丁醇 为溶剂， 生成 2,2-dimethyl-1-ferrocenyl-but-3-en-1-ol
  参考文献：
  名称：

  Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

  摘要：

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.

  DOI：

  10.1002/anie.202403073

文献信息

• Synthesis of ferrocenes with ene-terminus via water-promoted Barbier-like carbonyl allylation using bimetallic copper(II)/tin(II) reagent
  作者：Paromita Debroy、Sujit Roy

  DOI：10.1016/s0022-328x(03)00205-5

  日期：2003.5

  Fc[CH2C(R2)CH(R1)CH-μ(O)-CHCH(R1)C(R2)CH2] (8–11). The latter appear to result from the dehydration of intermediate homoallylic alcohols. Dehydration could be arrested in case of reaction of 1 and 2 with 1-bromo-3-methyl-but-2-ene, which results in the formation of homoallylic alcohols FcCH(OH)C(Me2)CHCH2 (7) and Fc[CH(OH)C(Me2)CHCH2]2 (12), respectively. All the reactions completely fail in absence of water.

  在二氯甲烷-水（1：1）中，在二水合氯化亚锡和催化氯化铜的存在下，甲酰二茂铁（1）与烯丙基溴的Barbier型γ-区域特异性烯丙基化，得到相应的二茂铁二烯FcCHC（R 1）C（R 2）CH 2（3 - 6）。另一方面，1,1'-双甲酰基二茂铁（2）的相似反应产生了具有烯丙基侧基Fc [CH 2 C（R 2）CH（R 1）CH-μ（O ）CHCH（R 1）C（R 2）CH 2 ]（8 - 11）。后者似乎是由中间均丙醇的脱水引起的。在1和2与1-溴-3-甲基-丁-2-烯反应的情况下，可以阻止脱水，这导致形成均丙醇FcCH（OH）C（Me 2）CHCH 2（7）和分别为Fc [CH（OH）C（Me 2）CHCH 2 ] 2（12）。在没有水的情况下，所有反应完全失败。
• Debroy, Paromita; Roy, Sujit, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2003, vol. 42, # 9, p. 2416 - 2421
  作者：Debroy, Paromita、Roy, Sujit

  DOI：——

  日期：——