isomentholactone | 68330-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: isomentholactone
• 英文别名: (4R,7R)-4-methyl-7-propan-2-yloxepan-2-one
• CAS: 68330-68-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: GGAXPLCKKANQED-RKDXNWHRSA-N

物化性质

• 沸点：
  248.3±8.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  isomentholactone 在 二异丁基氢化铝 、 水 作用下， 以 二氯甲烷 、 甲苯 、 四氢呋喃 为溶剂， 以98%的产率得到(3R,6R)-6-hydroxy-3,7-dimethyloctanal
  参考文献：
  名称：

  Low-temperature reduction of acyclic (–)-mentholactone derivatives with diisobutylaluminum hydride in methylene chloride

  摘要：

  Low-temperature treatment of acyclic (-)-mentholactone derivatives with excess diisobutylaluminum hydride in methylene chloride afforded O-isobutyl derivatives of seven-membered lactols. Methyl 6-hydroxy-3,7-dimethyloctanoate behaved similarly to (-)-mentholactone, and its 6-oxo analog, similarly to (-)-mentholactone and isomentholactone.

  DOI：

  10.1134/s1070428015070106
• 作为产物：
  描述：

  (+)-异薄荷醇 在 cyclic chromate ester C₇H₁₄CrO₄ 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到isomentholactone
  参考文献：
  名称：

  通过串联氧化-Baeyer-Villiger序列，将一元醇方便地一锅转化为酯

  摘要：

  A one-pot reaction sequence has been developed which converts secondary alcohols to esters via oxidation to the carbonyl compound and concomitant Baeyer-Villiger reaction. This procedure employs meta-chloroperoxybenzoic acid (mCPBA) as the primary oxidant in both steps and a catalytic amount of a cyclic Cr(VI) ester as a co-oxidant in the initial step. Isolated yields are typically very high and chromatographic purification of the crude product is often unnecessary for routine operations.

  DOI：

  10.1016/0040-4039(92)89009-2

文献信息

• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• Origin of High Diastereoselectivity in Reactions of Seven‐Membered‐Ring Enolates
  作者：Olga Lavinda、Collin H. Witt、K. A. Woerpel

  DOI：10.1002/anie.202114183

  日期：2022.3.28

  The diastereoselective reactions of chiral seven-membered-ring enolates have been systematically investigated. Diastereoselectivity was found to be general for ϵ-lactams, ϵ-lactones, and cycloheptanones with various substituent patterns. Computational investigations provided insight into the origin of the diastereoselectivity. A model for predicting the stereochemistry of seven-membered-ring enolate

  手性七元环烯醇化物的非对映选择性反应已被系统研究。发现对于具有各种取代基模式的ε-内酰胺、ε-内酯和环庚酮来说，非对映选择性是普遍的。计算研究提供了对非对映选择性起源的深入了解。提出了预测七元环烯醇化物烷基化立体化学的模型。
• Oxidative Cleavage of Methyl Ethers Using the HOF.cntdot.CH3CN Complex
  作者：Shlomo Rozen、Sharon Dayan、Yifat Bareket

  DOI：10.1021/jo00130a029

  日期：1995.12

  HOF . CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers. Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation. The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bend alpha to the ether moiety. It was found that the more sterically hindered is the C-H bond in question, the slower the reaction. In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place. When labeled (HOF)-O-18 . CH3CN is used on a O-16 methyl ether, the resulting ketone possesses only the heavier oxygen isotope. Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.
• Remote asymmetric induction. A stereoselective approach to acyclic diols via cyclic hydroboration
  作者：W. Clark Still、Kevin P. Darst

  DOI：10.1021/ja00544a049

  日期：1980.11
• Reduction at low temperature of isomentholactone with diisobutylaluminum hydride in CH2Cl2
  作者：G. Yu. Ishmuratov、V. A. Vydrina、Yu. A. Galkina、M. P. Yakovleva、R. R. Muslukhov、L. V. Kravchenko、D. Sh. Sabirov、A. G. Tolstikov

  DOI：10.1134/s1070428015080205

  日期：2015.8