丁位壬内酯 | 6008-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 丁位壬内酯
• 英文名称: oxecan-2-one
• 英文别名: 1-Oxacyclodecan-2-one；nonalactone；9-nonanolide；Oxecan-2-on；nonanoic lactone
• CAS: 6008-27-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: FTXUQEKXCJSWMO-UHFFFAOYSA-N

物化性质

• 沸点：
  220.47°C (rough estimate)
• 密度：
  0.9188 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  丁位壬内酯 在 三乙基硼氢化锂 作用下， 以 various solvent(s) 为溶剂， 反应 0.42h， 生成 1-壬醇
  参考文献：
  名称：

  Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations

  摘要：

  The enthalpies of hydrolysis of the monocyclic lactones from gamma-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl esters having the same number of atoms were studied in the same fashion. The enthalpies of reduction of the lactones to the corresponding alpha,omega-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the cases of gamma-butyrolactone and delta-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of gamma-butyrolactone and delta-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.

  DOI：

  10.1021/ja00020a036
• 作为产物：
  描述：

  8-溴辛酸 在 六甲基磷酰三胺 、 dimethyl sulfide borane 、 collidinium p-toluene sulfonate 、 Sensitox 、 四丁基氟化铵 、 氧气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 丁位壬内酯
  参考文献：
  名称：

  合成中的单线态氧。恶唑为羰基1,1-偶极子合成子。

  摘要：

  如7-庚醇化物，α-苄氧基δ-戊内酯和9-壬醇化物的合成所示，已将2，5-二苯基恶唑按两步顺序用作羰基1，1-偶极合成子。4-锂硫基-2，5-二苯基恶唑的烷基化，然后单线态氧氧化，产生三酰胺，该三酰胺经历环化成内酯。

  DOI：

  10.1016/s0040-4039(00)60874-2

文献信息

• Scandium Trifluoromethanesulfonate as an Extremely Active Lewis Acid Catalyst in Acylation of Alcohols with Acid Anhydrides and Mixed Anhydrides
  作者：Kazuaki Ishihara、Manabu Kubota、Hideki Kurihara、Hisashi Yamamoto

  DOI：10.1021/jo952237x

  日期：1996.1.1

  is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic activity of scandium triflate can be used for assisting the acylation by acid anhydrides of not only primary alcohols but also sterically-hindered secondary

  可商购的三氟甲磺酸（三氟甲磺酸late）是一种实用且有用的路易斯酸催化剂，用于在对硝基苯甲酸酐的存在下将醇与酸酐酰化或将醇通过羧酸酯化。三氟甲磺酸scan的极高的催化活性可用于协助伯醇的酸酐酰化以及空间受阻的仲或叔醇的酸酐酰化。所提出的方法对于ω-羟基羧酸的选择性大内酯化特别有效。
• A New Synthetic Method of Macrocylic Lactones from ω-Iodoalkylacrylates
  作者：Motoji Abe、Takaoki Hayashikoshi、Takeo Kurata

  DOI：10.1246/cl.1994.1789

  日期：1994.10

  When the photostimulated cyclization reaction of ω-iodoalkylacrylates was performed in the presence of metal hydride complexes such as sodium cyanoborohydride(NaBH3CN), sodium borohydride(NaBH4) and potassium borohydride(KBH4), the corresponding macrocyclic lactones were produced. The use of NaBH3CN led to the highest yield of lactones.

  当在氰基硼氢化钠(NaBH3CN)、硼氢化钠(NaBH4)和硼氢化钾(KBH4)等金属氢化物配合物存在下进行ω-碘代烷基丙烯酸酯的光刺激环化反应时，生成了相应的大环内酯。NaBH3CN 的使用导致内酯的最高产率。
• Vielgliedrige heterocyclische Verbindungen VIII. Zur Kenntnis der hochgliedrigen Mono- und Poly-lȧctonringe
  作者：M. Stoll、A. Rouvé

  DOI：10.1002/hlca.193501801153

  日期：——

  1. Es wurde gezeigt, dass die der Veresterungsreaktion entgegenlaufende Verseifungsreaktion keine messbare Geschwindigkeit besitzt.

  1.《世界经济日报》，《世界经济日报》。
• A Highly Efficient Macrolactonization Method via Ethoxyvinyl Ester
  作者：Yusuke Ohba、Mayuko Takatsuji、Kenji Nakahara、Hiromichi Fujioka、Yasuyuki Kita

  DOI：10.1002/chem.200801548

  日期：2009.3.23

  Facile and efficient macrolactonization of hydroxycarboxylic acid via ethoxyvinyl esters (EVEs), which can give 9‐ to 14‐membered macrolactones in good yields, has been developed (see scheme; DCE = 1,2‐dichloroethane). The method is useful for acid‐/base‐sensitive substrates and applicable to the compound with many functional groups.

  已经开发了通过乙氧基乙烯基酯（EVE）进行羟基羧酸的简便有效的大环内酯化反应，该酯能以良好的收率生成9至14元大环内酯（请参阅方案； DCE = 1,2-二氯乙烷）。该方法适用于酸/碱敏感底物，适用于具有许多官能团的化合物。
• Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity
  作者：Kei Takeda、Ikuhiro Imaoka、Eiichi Yoshii

  DOI：10.1016/s0040-4020(01)85696-9

  日期：1994.1

  Diels-Alder reaction of 1,6-bis(trimethylsilyloxy)-2,4-hexadiene with α-substituted acrylates and 5 to 7- and 9 to 11-membered α-(methylene)lactones has been carried out to examine correlation of dienophile structure with endo/exo selectivity. While the conformationally flexible acrylates produced cycloadducts of endo/exo = 59:41 to 74:26, the 5 to 7-membered lactones with rigid s-cis conjugate system

  1,6-双（三甲基甲硅烷氧基）-2,4-己二烯与α-取代的丙烯酸酯以及5至7和9至11元的α-（亚甲基）内酯的Diels-Alder反应已经进行，以检验亲二烯体的相关性具有内/外选择性的结构。构象柔性丙烯酸酯可生成内/外环的加合物= 59:41至74:26，具有刚性s-顺式共轭体系的5至7元内酯可提供内/外环的13:87至32:68的高聚物。可以同时具有s-顺式和s-反式构象的9至11元内酯提供的内/外比为37:63至57:43。