3-methyl-1-oxaspiro<4.5>decan-2-one | 16149-84-1

• 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: 3-methyl-1-oxaspiro<4.5>decan-2-one
• 英文别名: 3-Methyl-1-oxaspiro[4.5]decan-2-one
• CAS: 16149-84-1；350010-19-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: SGVAFCFCMZMLBI-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  266.3±8.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  3-methyl-1-oxaspiro<4.5>decan-2-one 在 甲烷磺酸 、 phosphorus pentoxide 作用下， 以76%的产率得到8-methylbicyclo[4.3.0]non-1⁶-en-7-one
  参考文献：
  名称：

  Three carbon annelation reagents: unsaturated alpha aminonitriles as homoenolate equivalents

  摘要：

  DOI：

  10.1016/s0040-4039(00)71371-2
• 作为产物：
  描述：

  trans-(+/-)-4-cyclohexyl-3-methyloxetan-2-one 在 magnesium bromide 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以75%的产率得到3-methyl-1-oxaspiro<4.5>decan-2-one
  参考文献：
  名称：

  Dyotropic rearrangement of cycloalkyl .beta.-lactones. Formation of spiro versus fused butyrolactones as a function of ring size

  摘要：

  DOI：

  10.1021/jo00260a021

文献信息

• Selective Mono- and Bis(alkoxycarbonylation)s of Olefins Catalyzed by Palladium in the Presence of Cu(I) or Cu(II) Chloride under Remarkably Mild Conditions. Application to the Synthesis of γ-Butyrolactone Derivatives
  作者：Shiho Toda、Masanori Miyamoto、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/bcsj.64.3600

  日期：1991.12

  Palladium-catalyzed mono- and bis(alkoxycarbonylation)s of olefins were controlled by the use of copper(II) and copper(1) chloride, respectively, in alcohol under normal pressure of carbon monoxide and oxygen at room temperature without any other additives. 3-Buten-1-ols gave the corresponding γ-butyrolactones and 2-oxotetrahydrofuran-3-acetic acid esters, respectively, in high yields.

  在室温下、正常压力的二氧化碳和氧气环境下，使用铜(II)和铜(I)氯化物分别控制钯催化的单和双(烷氧基羰基化)反应，无需其他添加剂即可使烯烃产生反应。3-丁烯-1-醇则分别高效地生成相应的γ-丁酰内酯和2-氧杂四氢呋喃-3-乙酸酯。
• Reductive coupling of ketones or aldehydes with electron-deficient alkenes promoted by samarium di-iodide
  作者：Shin-ichi Fukuzawa、Akira Nakanishi、Tatsuo Fujinami、Shizuyoshi Sakai

  DOI：10.1039/c39860000624

  日期：——

  Samarium di-iodide is an efficient reagent for the reductive coupling of ketones or aldehydes and electron-deficient alkenes, whereby γ-lactones can be prepared in good yields from ethyl acrylate.

  io二碘化物是一种有效的试剂，用于酮或醛与电子缺乏的烯烃的还原偶联，从而可以由丙烯酸乙酯高收率地制备γ-内酯。
• A new synthesis of substituted spiro butyrolactones via dyotropic rearrangement
  作者：T.Howard Black、William J. DuBay

  DOI：10.1016/s0040-4039(00)96625-5

  日期：1987.1

  Spiro butyrolactones bearing various α-substituents have been synthesized in three steps from acetic acid derivatives; the sequence employs a dyotropic rearrangement as its pivotal step.

  由乙酸衍生物分三步合成了带有各种α-取代基的螺丁内酯。该序列采用发散重排作为其关键步骤。
• New synthesis and reactions of [Sm(OTf)2(DME)2], a salt-free samarium(II) triflate
  作者：Jacqueline Collin、Nicolas Giuseppone、Fouzia Machrouhi、Jean-Louis Namy、François Nief

  DOI：10.1016/s0040-4039(99)00417-7

  日期：1999.4

  new, simple and high-yield synthesis of a salt-free samarium(II) triflate, [Sm(OTf)2(DME)2] is described. In stoichiometric amounts this derivative mediates typical samarium (II) coupling reactions such as pinacolisation, dimerisation of imines and Barbier-type reactions. It can also acts as a precatalyst for Mukaiyama aldol and Michael reactions and Diels-Alder reactions.

  描述了一种新的，简单且高收率的无盐三氟甲磺酸sa [Sm（OTf）2（DME）2 ]合成方法。以化学计量的量，该衍生物介导典型的（（II）偶联反应，例如频哪醇化，亚胺的二聚化和Barbier型反应。它也可以作为Mukaiyama aldol和Michael反应以及Diels-Alder反应的预催化剂。
• Asymmetric Bis(alkoxycarbonylation) Reaction of Homoallylic Alcohols Catalyzed by Palladium in the Presence of Cu(I) Triflate Using the Chiral Bioxazoline Ligand
  作者：Yutaka Ukaji、Masanori Miyamoto、Miho Mikuni、Susumu Takeuchi、Katsuhiko Inomata

  DOI：10.1246/bcsj.69.735

  日期：1996.3

  Palladium-catalyzed asymmetric intra- and intermolecular bis(alkoxycarbonylation) reactions of homoallylic alcohols in the presence of copper(I) triflate were achieved by using the chiral bioxazoline ligand, (S,S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 °C to give the corresponding optically active γ-butyrolactones in 19—65% ee.

  利用手性二噁唑啉配体，在三酸铜（I）存在下实现了钯催化的均烯醇分子内和分子间不对称双（烷氧基羰基化）反应、(S,S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole 手性二噁唑啉配体，在一氧化碳和氧气的常压下于 25 °C，得到相应的光学活性 γ-丁内酯，ee 为 19-65%。