2-methylcyclopent-2-en-1-yl acetate | 92984-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylcyclopent-2-en-1-yl acetate
• 英文别名: acetic acid-(2-methyl-cyclopent-2-enyl ester)；Essigsaeure-(2-methyl-cyclopent-2-enylester)；(+/-)-(2-Methyl-cyclopenten-(2)-yl)-acetat；(+/-)-5-Acetoxy-1-methyl-cyclopenten-(1)；(2-Methylcyclopent-2-en-1-yl) acetate
• CAS: 92984-84-4
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: NSKPZYVFBWKOBL-UHFFFAOYSA-N

物化性质

• 沸点：
  168.2±29.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylcyclopent-2-en-1-yl acetate 在 chromium(VI) oxide 、 sodium hydroxide 、 水 作用下， 生成 甲基环戊烯醇酮
  参考文献：
  名称：

  Dane et al., Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 39,47

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基环戊烯醇酮 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-methylcyclopent-2-en-1-yl acetate
  参考文献：
  名称：

  The influence of remote heteroatom substituents on the stereoselectivity of cyclopentene ozonolysis

  摘要：

  The stereoselectivity for ozonide formation from cyclopentenes with allylic heteroatom substituents has been examined. Silyl ethers give high selectivity in favor of the exo-substituted ozonide, while esters of 2-cyclopentenol form ozonide mixtures with little stereoselection. Trapping experiments establish that fragmentation of the primary ozonides is highly regioselective to give only one of the isomeric omega-oxo carbonyl oxide intermediates and that the variation in final ozonide stereochemistry results from differing interactions between the remote substituent groups and the carbonyl oxide system during cyclization of this intermediate. The effect of substituent and solvent on ozonide stereochemistry suggests a dominant role for electrostatic repulsion between carbonyl oxide and the heteroatom substituent during intramolecular cycloaddition. A chair-like transition state is proposed for this process and is in accord with the increase in exo selectivity for derivatives of 2-methyl-2-cyclopentenol.

  DOI：

  10.1021/jo00028a059

文献信息

• Asymmetric Ring-Closing Metathesis Catalyzed by Chiral Molybdenum Alkylidene Complexes
  作者：Osamu Fujimura、Robert H. Grubbs

  DOI：10.1021/jo971952z

  日期：1998.2.1

  2-bis(2'-hydroxyethyl)cyclohexane). In the case of a prochiral symmetric triene substrate, optically active cyclized product was formed by catalytic ring-closing metathesis with 1, which opens the possibility of a new version of two-directional synthesis. Although the observed enantiomeric excesses were modest to low, this data demonstrates the feasibility of asymmetric induction by chiral alkylidene catalysts

  在新开发的手性钼亚烷基络合物（R，R）-Mo（CHCMe（2）Ph）（NAr）（TBEC）1（Ar = 2,6-i）催化下，外消旋二烯的闭环易位反应中观察到动力学拆分-Pr（2）C（6）H（3），TBEC = 2'，2'，2“，2”-四（三氟甲基）-1,2-双（2'-羟乙基）环戊烷）和（R， R）-Mo（CHCMe（2）Ph）（NAr）（TBEH）2（Ar = 2,6-i-Pr（2）C（6）H（3），TBEH = 2'，2'，2“ ，2″-四（三氟甲基）-1，2-双（2′-羟乙基）环己烷）。在前手性对称三烯底物的情况下，光学活性环化产物是通过催化闭环复分解反应与1形成的，这为双向合成的新形式打开了可能性。尽管观察到的对映体过量适度至低，
• Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates
  作者：Santanu Panda、Joseph M. Ready

  DOI：10.1021/jacs.7b01410

  日期：2017.5.3

  The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

  硼酸酯与2-锂化的吲哚反应形成硼酸酯中间体。硼酸酯在（BINAP）Pd催化剂存在下与乙酸烯丙酯反应，使C3烯丙基化，同时烷基从吲哚的B迁移至C2。总体而言，该过程是三组分偶联，将乙酸烯丙酯，吲哚和有机B（pin）物种连接在一起，以提供具有高对映体，区域和非对映选择性的取代的吲哚和吲哚。
• Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+-.)-hirsutene
  作者：Dennis P. Curran、Donna M. Rakiewicz

  DOI：10.1021/ja00291a077

  日期：1985.3

  Synthese a partir de la methyl-6a tetrahydro cyclopenta [b] furannone-2, avec comme etape cle la cyclisation d'un iodoalkyl alcynyl cyclopentene intermediaire

  合成 a partir de lamethyl-6a 四氢环戊烷 [b] furannone-2, avec comme etape cle la cyclisation d'un iodoalkyl alcynyl cyclopentene intermediaire
• Preparation of allylic acetates from simple alkenes by palladium(II)-catalyzed acetoxylation
  作者：Sverker Hansson、Andreas Heumann、Tobias Rein、Bjoern Aakermark

  DOI：10.1021/jo00290a031

  日期：1990.2
• Optically active cyclopentenols and process for preparing the same
  申请人：Chisso Corporation

  公开号：EP0414453B1

  公开（公告）日：1994-02-23