8-hydroxynonanoic acid lactone | 82120-79-4

• 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: 8-hydroxynonanoic acid lactone
• 英文别名: 9-methyloxonan-2-one；8-methyloctalactone；(+/-)-8-Nonanolide；8-Methyloctanolactone
• CAS: 82120-79-4
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: XJUMADFCBHRJQU-UHFFFAOYSA-N

物化性质

• 沸点：
  255.1±8.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-hydroxynonanoic acid lactone 在 sodium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 生成 ((1S,9S)-10-Chloro-3-methyl-2-oxa-bicyclo[7.1.0]dec-1-yloxy)-trimethyl-silane
  参考文献：
  名称：

  Iterative synthesis of selectively substituted .alpha.,.beta.-unsaturated and saturated medium-ring lactones

  摘要：

  DOI：

  10.1021/jo00303a010
• 作为产物：
  描述：

  2-甲基环辛烷-1-酮 在 disodium hydrogenphosphate 、 三氟过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到8-hydroxynonanoic acid lactone
  参考文献：
  名称：

  大环化合物构象的化学后果：远程不对称诱导的有效方法1

  摘要：

  在本文中，我们表明中环和大环有机分子的构象性质对其化学反应的立体化学过程具有深远的影响。在各种单取代的8至12元大环酮和内酯上检查了动力学烯醇烷基化，二甲基cup酸酯的添加和催化氢化，并确定了产物的非对映异构体组成。在许多系统中，单个Me取代基提供了足够的构象偏差，可以高度立体选择性地形成新的不对称中心。

  DOI：

  10.1016/s0040-4020(01)93273-9

文献信息

• [EN] MACROCYCLIC PICOLINAMIDES AS FUNGICIDES<br/>[FR] PICOLINAMIDES MACROCYCLIQUES À UTILISER EN TANT QUE FONGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017116956A1

  公开（公告）日：2017-07-06

  This disclosure relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.

  这份公开信息涉及公式(I)的宏观环状吡啶酰胺及其作为杀菌剂的使用。
• Chemical consequences of conformation in macrocyclic compounds
  作者：W.Clark Still、Igor Galynker

  DOI：10.1016/s0040-4020(01)93273-9

  日期：——

  In this paper we show that the conformational properties of medium- and large-ring organic molecules have profound consequences on the stereochemical course of their chemical reactions. Kinetic enolate alkylations, dimethylcuprate additions and catalytic hydrogenations were examined on a variety of monosubstituted 8- to 12-membered macrocyclic ketones and lactones, and the diastereomeric composition

  在本文中，我们表明中环和大环有机分子的构象性质对其化学反应的立体化学过程具有深远的影响。在各种单取代的8至12元大环酮和内酯上检查了动力学烯醇烷基化，二甲基cup酸酯的添加和催化氢化，并确定了产物的非对映异构体组成。在许多系统中，单个Me取代基提供了足够的构象偏差，可以高度立体选择性地形成新的不对称中心。
• Efficient synthesis of (R)-harmonine – the toxic principle of the multicolored Asian lady beetle (Harmonia axyridis)
  作者：Nadja C. Nagel、Anita Masic、Uta Schurigt、Wilhelm Boland

  DOI：10.1039/c5ob00461f

  日期：——

  An efficient and flexible synthesis of (R)-harmonine and putative biosynthetic precursors has been developed. Furthermore, its antimicrobial activity againstLeishmania majoris demonstrated.

  一种高效灵活的合成方法已经开发出来，用于合成（R）-harmonine和可能的生物合成前体。此外，已证明其对Leishmania major的抗微生物活性。
• [EN] 1,2,4,-TRIOXEPANES AS PRECURSORS FOR LACTONES<br/>[FR] 1,2,4,-TRIOXEPANES UTILES EN TANT QUE PRECURSEURS POUR DES LACTONES
  申请人：AKZO NOBEL NV

  公开号：WO2005014569A1

  公开（公告）日：2005-02-17

  The present invention pertains to a novel process for the preparation of lactones by decomposition of a 1,2,4-­trioxepane of formula (I) wherein, R is H or CH3, n is 1-14, Rx independently is any substituent on the ring structure, including substituents which form bi- or tricyclic structures, and m is 0-34.

  本发明涉及一种新型的制备内酯的方法，通过分解式(I)中的1,2,4-三氧杂环庚烷，其中，R为H或CH3，n为1-14，Rx独立地是环结构上的任何取代基，包括形成双环或三环结构的取代基，m为0-34。
• Switching from <i>S</i>- to <i>R-</i>Selectivity in the <i>Candida </i><i>antarctica</i> Lipase B-Catalyzed Ring-Opening of ω-Methylated Lactones:  Tuning Polymerizations by Ring Size
  作者：Jeroen van Buijtenen、Bart A. C. van As、Marloes Verbruggen、Luc Roumen、Jef A. J. M. Vekemans、Koen Pieterse、Peter A. J. Hilbers、Lumbertus A. Hulshof、Anja R. A. Palmans、E. W. Meijer

  DOI：10.1021/ja071241a

  日期：2007.6.13

  Novozym 435-catalyzed ring-opening of a range of omega-methylated lactones demonstrates fascinating differences in rate of reaction and enantioselectivity. A switch from S- to R-selectivity was observed upon going from small (ring sizes <= 7) to large lactones (ring sizes >= 8). This was attributed to the transition from a cisoid to a transoid conformational preference of the ester bond on going from small to large lactones. The S-selectivity of the ring-opening of the small, cisoid lactones was low to moderate, while the R-selectivity of the ring-opening of the large transoid lactones was surprisingly high. The S-selectivity of the ring-opening of the small, cisoid lactones combined with the established R-selectivity of the transesterification of (aliphatic) secondary alcohols prevented polymerization from taking place. Ring-opening of the large, transoid lactones was R-selective with high enantioselectivity. As a result, these lactones could be polymerized, without exception, by straightforward kinetic resolution polymerization, yielding the enantiopure R-polyester with excellent enantiomeric excess (>99%).