2,2-Dimethyl-3,4-pentadien-1-ol | 4058-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-3,4-pentadien-1-ol
• 英文别名: 2,2-dimethyl-penta-3,4-dien-1-ol；2.2-Dimethyl-pentadien-(3.4)-ol-(1)；2,2-Dimethylpenta-3,4-dien-1-ol；2,2-Dimethyl-penta-3,4-dienol；3,4-Pentadien-1-ol, 2,2-dimethyl-
• CAS: 4058-52-0
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: NOTNXVNZHXXZSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2,2-Dimethyl-3,4-pentadien-1-ol 反应 0.5h， 生成 3,3,5-trimethyl-2H-furan
  参考文献：
  名称：

  Alkaline Earth Catalysis of Alkynyl Alcohol Hydroalkoxylation/Cyclization

  摘要：

  Heavier alkaline earth bis(trimethylsilyl)amides [Ae{N(SiMe3)(2)}(2)](2) (Ae = Ca, Sr, Ba) are shown to act as effective precatalysts for the regioselective intramolecular hydroalkoxylation/cyclization of a wide range of alkynyl and allenyl alcohols. In the majority of cases, cyclization of alkynyl alcohols produces mixtures of the possible endo- and exocyclic enol ether products, rationalized as a consequence of alkynylalkoxide isomerization to the corresponding allene derivatives. Cyclization rates for terminal alkynyl alcohols were found to be significantly higher than for substrates bearing internal alkynyl substituents, while the efficacy of cyclization was in general found to be determined by a combination of stereoelectronic influences and the thermochemical viability of the specific alkaline earth metal catalysis, which we suggest is determined by the individual M-O bond strengths. Kinetic studies have provided a rate law pertaining to a pronounced catalyst inhibition with increasing [substrate], indicating that turnover-limiting insertion of C-C unsaturation into the M-O bond requires the dissociation of substrate molecules away from the Lewis acidic alkaline earth center.

  DOI：

  10.1021/om3008663
• 作为产物：
  描述：

  2,2-二甲基戊-3,4-二烯醛 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2,2-Dimethyl-3,4-pentadien-1-ol
  参考文献：
  名称：

  Unsaturated neopentyl compounds. Homoallenyl participation in the acetolysis of 2,2-dimethyl-3,4-pentadienyl p-bromobenzenesulfonate

  摘要：

  DOI：

  10.1021/ja01002a030

文献信息

• Allene Epoxidation. Highly functionalized tetrahydrofurans and tetrahydropyrans from the oxidative cyclization of allenic alcohols.
  作者：Jack K. Crandall、David J. Batal、Feng Lin、Thierry Reix、Gregory S. Nadol、Raymond A. Ng

  DOI：10.1016/s0040-4020(01)92232-x

  日期：1992.2

  The dimethyldioxirane oxidation of various allenic alcohols yields highly functionalized tetrahydrofuran and tetrahydropyran derivatives via intramolecular nucleophilic addition of the hydroxy group to an intermediate allene diepoxide.

  各种烯丙醇的二甲基二环氧乙烷烷氧化通过将羟基分子内亲核加成到中间烯丙基二环氧化合物上而得到高度官能化的四氢呋喃和四氢吡喃衍生物。
• Allene epoxidation. Oxidative cyclizations of allenyl alcohols.1
  作者：Jack K. Crandall、David J. Batal

  DOI：10.1016/s0040-4039(00)80610-3

  日期：1988.1

  The dimethyldioxirane oxidation of various allenic alcohols yields highly functionalized tetrahydrofuran and tetrahydropyran derivatives via intramolecular nucleophilic addition of the hydroxy group to an intermediate allene diepoxide.

  各种烯丙醇的二甲基二环氧乙烷烷氧化通过将羟基分子内亲核加成到中间烯丙基二环氧化合物上而得到高度官能化的四氢呋喃和四氢吡喃衍生物。
• Decarbopalladation of π-Allylpalladium Intermediates Formed from Palladium-Catalyzed Arylations of 3-Allen-1-ols
  作者：Chang Ho Oh、Seung Hyun Jung、Su Youn Bang、Dai In Park

  DOI：10.1021/ol026659m

  日期：2002.9.1

  Unusual palladium-catalyzed arylative fragments of acyclic 3-alien-1-ols were observed. Oxidative addition of Pd(0) to aryl halides would form the arylpalladium halides, which added to the central carbon of allenes via carbopalladation to form the pi-allylpalladium intermediates. The pi-allylpalladium intermediates would be reductively eliminated via carbon-carbon cleavage to give the arylated dienes and the alpha-hydroxyalkylpalladium intermediates, which were further reductively eliminated to the corresponding aldehydes.
• Anchimeric assistance, rearrangement, and solvent addition in the formolysis of a nonconjugated acetylenic (homopropargylic) tosylate
  作者：Joseph William Wilson

  DOI：10.1021/ja01040a025

  日期：1969.6
• CRANDALL, JACK K.;BATAL, DAVID J., TETRAHEDRON LETT., 29,(1988) N 38, C. 4791-4794
  作者：CRANDALL, JACK K.、BATAL, DAVID J.

  DOI：——

  日期：——