(R)-6,10-dimethyl-9-undecen-2-one | 114976-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-6,10-dimethyl-9-undecen-2-one
• 英文别名: (6R)-5,6-dihydrogeranyl acetone；(6R)-6,10-dimethylundec-9-en-2-one；(R)-6,10-dimethylundec-9-en-2-one；(R)-6,10-dimethyl-9-undecene-2-one
• CAS: 114976-95-3
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: LGVYUZVANMHKHV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-6,10-dimethyl-9-undecen-2-one 在 氨 、 lithium 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 27.5h， 生成 (3RS,7R)-3,7,11-trimethyl-10-dodecen-1-ol
  参考文献：
  名称：

  Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: application to enantiomeric syntheses of tribolure and a marine fatty acid

  摘要：

  DOI：

  10.1016/s0957-4166(02)00365-8
• 作为产物：
  描述：

  (S)-(-)-β-香茅醇 在 吡啶 、 溴 、 三苯基膦 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-6,10-dimethyl-9-undecen-2-one
  参考文献：
  名称：

  Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: application to enantiomeric syntheses of tribolure and a marine fatty acid

  摘要：

  DOI：

  10.1016/s0957-4166(02)00365-8

文献信息

• Hydrogenation process
  申请人：Hoffmann-La Roche, Inc.

  公开号：US05132464A1

  公开（公告）日：1992-07-21

  There is disclosed a catalytic hydrogenation process resulting in compounds of the formula ##STR1## wherein the dotted line represents a facultative bond, by hydrogenating the compound of the formula ##STR2## in the presence of a platinum or a nickel catalyst.

  本发明涉及一种催化加氢过程，通过在铂或镍催化剂存在下，对式为##STR2##的化合物进行加氢，得到式为##STR1##的化合物，其中虚线表示可选键。
• Synthesis and Biological Evaluation of Aurachin D Analogues as Inhibitors of <i>Mycobacterium tuberculosis</i> Cytochrome <i>bd</i> Oxidase
  作者：Aggie Lawer、Chelsea Tyler、Kiel Hards、Laura M. Keighley、Chen-Yi Cheung、Fabian Kierek、Simon Su、Siddharth S. Matikonda、Tyler McInnes、Joel D. A. Tyndall、Kurt L. Krause、Gregory M. Cook、Allan B. Gamble

  DOI：10.1021/acsmedchemlett.2c00401

  日期：2022.10.13

  A revised total synthesis of aurachin D (1a), an isoprenoid quinolone alkaloid that targets Mycobacterium tuberculosis (Mtb) cytochrome bd (cyt-bd) oxidase, was accomplished using an oxazoline ring-opening reaction. The ring opening enabled access to a range of electron-poor analogues, while electron-rich analogues could be prepared using the Conrad–Limpach reaction. The aryl-substituted and side-chain-modified

  aurachin D ( 1a ) 是一种类异戊二烯喹诺酮生物碱，靶向结核分枝杆菌( Mtb ) 细胞色素bd (cyt- bd ) 氧化酶，使用恶唑啉开环反应完成了修订的全合成。开环使得能够获得一系列贫电子类似物，而富电子类似物可以使用康拉德-林帕奇反应来制备。筛选了芳基取代和侧链修饰的金豆素 D 类似物，以抑制Mtb细胞色素-bd氧化酶和抑制Mtb生长。观察到短链类似物1d（香茅基侧链）和芳基取代类似物1g / 1k（C6/C7 处的氟取代基）、1t / 1v（C5/C6 处的羟基取代基）对Mtb cyt - bd氧化酶的纳摩尔抑制) 和1u / 1w / 1x (C5/C6/C7 处的甲氧基取代基)。Aurachin D 及其类似物不会抑制非致病性耻垢分枝杆菌的生长，但Mtb cyt -bd氧化酶测定中的香茅基 ( 1d ) 和 6-氟取代 ( 1g ) 抑制剂对致病性Mtb表现出中等的生长抑制作用(MIC
• Aristolochene Synthase. Elucidation of the Cryptic Germacrene A Synthase Activity Using the Anomalous Substrate Dihydrofarnesyl Diphosphate
  作者：David E. Cane、Youla S. Tsantrizos

  DOI：10.1021/ja961981b

  日期：1996.1.1

  Germacrene A (3) has been proposed to be an intermediate in the cyclization of farnesyl diphosphate (1) to the sesquiterpene hydrocarbon (+)-aristolochene (2). Under normal circumstances, however, neither 3 nor any other intermediate is released from the cyclase active site. When the anomalous substrate (7R)-6,7-dihydrofarnesyl diphosphate (5) is incubated with aristolochene synthase from Aspergillus terreus, the resultant dihydrogermacrene (6) cannot be further cyclized and is released from the active site. The structure of the abortive cyclization product, mit 206, was confirmed as dihydrogermacrene (6) by direct CC-MS comparison with an authentic synthetic sample prepared from (-)-(3S)-beta-citronellol.
• Mori, Kenji; Igarashi, Yasuhiro, Liebigs Annalen der Chemie, 1988, p. 717 - 720
  作者：Mori, Kenji、Igarashi, Yasuhiro

  DOI：——

  日期：——
• Compositions and Methods to Attract the Brown Marmorated Stink Bug (BMSB), Halyomorpha halys
  申请人：Secretary of Agriculture United States of America as Represented by the

  公开号：US20140161764A1

  公开（公告）日：2014-06-12

  A composition (useful for attracting Halyomorpha halys ) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols:trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl(2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.