2-甲基十一烷-3-酮 | 6315-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基十一烷-3-酮
• 英文名称: 2-methylundecan-3-one
• 英文别名: 2-Methyl-undecan-3-on；Isopropyl-octyl-keton；Isopropyl-n-octyl-keton
• CAS: 6315-95-3
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: GFUKRKCQQBTCNT-UHFFFAOYSA-N

物化性质

• 熔点：
  -11.27°C (estimate)
• 沸点：
  243.3°C (estimate)
• 密度：
  0.8288 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  2-甲基十一烷-3-酮 在 乙醚 、 sodium 作用下， 生成 2-methyl-undecan-3-ol
  参考文献：
  名称：

  Pickard; Kenyon, Journal of the Chemical Society, 1912, vol. 101, p. 6295

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-undecane-2,3-diol 在 甲酸 作用下， 生成 2-甲基十一烷-3-酮
  参考文献：
  名称：

  Elphimoff-Scherbakoff, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 222, p. 597

  摘要：

  DOI：

文献信息

• One-carbon homologation of unsymmetrical ketones through magnesium β-oxido carbenoid rearrangement and trapping the enolate intermediates with electrophiles
  作者：Shu Tanaka、Takehiro Anai、Makoto Tadokoro、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2008.05.079

  日期：2008.7

  A procedure for one-carbon homologation of unsymmetrical ketones, including one-carbon ring-expansion of 2-substituted cyclohexanones, through magnesium β-oxido carbenoid rearrangement as the key reaction is described. Addition of the α-sulfinyl carbanion of 1-chloroethyl p-tolyl sulfoxide to an unsymmetrical ketone gave two diastereomers as adducts in good yields. The adducts were treated with a base

  描述了一种通过不对称酮的一碳同系化（包括2-取代的环己酮的一碳环扩展）通过镁β-氧化类胡萝卜素重排作为关键反应的方法。1-氯乙基p的α-亚磺酰基碳负离子的加成甲苯磺酸亚砜制得不对称酮后，以高收率得到了两种非对映异构体作为加合物。将加合物用碱处理以得到醇盐，将其用格氏试剂处理以得到β-氧化类胡萝卜素镁。然后进行β-氧化类胡萝卜素重排，以提供在α-位具有甲基的一碳同系酮。在重排中观察到显着的特异性或选择性。发现该反应的烯醇镁中间体能够被数种亲电试剂捕获，从而得到一碳同系的α，α-二取代的酮。还讨论了特异性和选择性的起源。
• ARYL DIHYDROPYRIDINONE AND PIPERIDINONE MGAT2 INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：US20130143843A1

  公开（公告）日：2013-06-06

  The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are monoacylglycerol acyltransferase type 2 (MGAT2) inhibitors which may be used as medicaments.

  本发明提供了以下式（I）的化合物： 或其立体异构体，或其药学上可接受的盐，其中所有变量如本文所定义。这些化合物是单酰基甘油酰基转移酶2（MGAT2）抑制剂，可用作药物。
• Rho-dependent inhibition of the induction of connective tissue growth factor (CTGF) by HMG CoA reductase inhibitors (statins)
  作者：Michael Eberlein、Juliane Heusinger-Ribeiro、Margarete Goppelt-Struebe

  DOI：10.1038/sj.bjp.0704173

  日期：2001.8

  It was supposed that inhibitors of 3‐hydroxy‐3‐methylglutaryl‐coenzyme A (HMG CoA) reductase (statins) might inhibit the expression of the fibrosis‐related factor CTGF (connective tissue growth factor) by interfering with the isoprenylation of Rho proteins. The human renal fibroblast cell line TK173 was used as an in vitro model system to study the statin‐mediated modulation of the structure of the actin cytoskeleton and of the expression of CTGF mRNA. Incubation of the cells with simvastatin or lovastatin time‐dependently and reversibly changed cell morphology and the actin cytoskeleton with maximal effects observed after about 18 h. Within the same time period, statins reduced the basal expression of CTGF and interfered with CTGF induction by lysophosphatidic acid (LPA) or transforming growth factor beta. Simvastatin and lovastatin proved to be much more potent than pravastatin (IC50 1–3 μM compared to 500 μM). The inhibition of CTGF expression was prevented when the cells were incubated with mevalonate or geranylgeranylpyrophosphate (GGPP) but not by farnesylpyrophosphate (FPP). Specific inhibition of geranylgeranyltransferase‐I by GTI‐286 inhibited LPA‐mediated CTGF expression whereas an inhibitor of farnesyltransferases FTI‐276 was ineffective. Simvastatin reduced the binding of the small GTPase RhoA to cellular membranes. The effect was prevented by mevalonate and GGPP, but not FPP. These data are in agreement with the hypothesis that interference of statins with the expression of CTGF mRNA is primarily due to interference with the isoprenylation of RhoA, in line with previous studies, which have shown that RhoA is an essential mediator of CTGF induction. The direct interference of statins with the synthesis of CTGF, a protein functionally related to the development of fibrosis, may thus be a novel mechanism underlying the beneficial effects of statins observed in renal diseases. British Journal of Pharmacology (2001) 133, 1172–1180; doi:10.1038/sj.bjp.0704173

  假设羟甲基戊二酰辅酶 A（HMG-CoA）还原酶抑制剂（他汀类药物）可能通过干扰 Rho 蛋白的牻牛儿基牻牛儿基化作用来抑制与纤维化相关的因子 CTGF（结缔组织生长因子）的表达。 以人肾成纤维细胞系 TK173 作为体外模型系统，研究他汀类药物介导的肌动蛋白细胞骨架结构以及 CTGF mRNA 表达的调控作用。 将细胞分别与辛伐他汀或洛伐他汀共同孵育，细胞形态及肌动蛋白细胞骨架在时间依赖性和可逆性变化下，约 18 小时时观察到最大效应。 在同一时间段内，他汀类药物降低了 CTGF 的基础表达，并干扰了 CTGF 由溶血磷脂酸（LPA）或转化生长因子 β 所诱导的表达。辛伐他汀和洛伐他汀的作用远强于普伐他汀（IC₅₀ 1–3 μM 与 500 μM 相比）。 当细胞与甲羟戊酸或牻牛儿基牻牛儿基二磷酸（GGPP）共同孵育时，CTGF 表达的抑制作用被逆转，而法尼基二磷酸（FPP）则无效。使用 GTI-286 特异性抑制牻牛儿基牻牛儿基转移酶 I 抑制了 LPA 介导的 CTGF 表达，而法尼基转移酶抑制剂 FTI-276 无效。 辛伐他汀降低了小 GTP 酶 RhoA 在细胞膜的结合。该作用被甲羟戊酸和 GGPP 阻断，但 FPP 无效。 数据支持他汀类药物通过干扰 RhoA 的牻牛儿基牻牛儿基化作用影响 CTGF mRNA 表达的假设，这与先前研究表明 RhoA 是 CTGF 诱导的关键介质一致。 他汀类药物直接干扰 CTGF（与纤维化相关蛋白质）合成，可能是在肾脏疾病中观察到的他汀类药物有益作用的新机制。 *《英国药理学杂志》* (2001), **133**, 1172–1180; **DOI:** [10.1038/sj.bjp.0704173](https://doi.org/10.1038/sj.bjp.0704173)
• Nickel-catalyzed cross-coupling of unactivated alkyl halides and tosylate carrying a functional group with alkyl and phenyl Grignard reagents
  作者：Surya Prakash Singh、Jun Terao、Nobuaki Kambe

  DOI：10.1016/j.tetlet.2009.07.094

  日期：2009.10

  primary and secondary alkyl Grignard reagents undergo cross-coupling with alkyl bromides, iodide, and tosylate carrying a functional group such as amide, ester, and ketone at 0 °C in THF. The present procedure provides a simple, convenient, and practical method for construction of carbon chains in the presence of various functional groups. PhMgBr also gave the corresponding coupling product in a moderate

  通过使用催化量的镍盐和1,3-丁二烯，伯氏和仲烷基格氏试剂与0处带有官能团（如酰胺，酯和酮）的烷基溴化物，碘化物和甲苯磺酸盐进行交叉偶联。在THF中为°C。本方法提供了在各种官能团存在下构建碳链的简单，方便和实用的方法。PhMgBr还以中等收率得到了相应的偶联产物。
• BIOFUEL PRODUCTION
  申请人：Yoshikuni Yasuo

  公开号：US20090139134A1

  公开（公告）日：2009-06-04

  Methods, enzymes, recombinant microorganism, and microbial systems are provided for converting polysaccharides, such as those derived from biomass, into suitable monosaccharides or oligosaccharides, as well as for converting suitable monosaccharides or oligosaccharides into commodity chemicals, such as biofuels. Commodity chemicals produced by the methods described herein are also provided. Commodity chemical enriched, refinery-produced petroleum products are also provided, as well as methods for producing the same.

  提供了用于将多糖转化为适当的单糖或寡糖的方法、酶、重组微生物和微生物系统，例如从生物质中提取的多糖。同时提供了将适当的单糖或寡糖转化为商品化学品，如生物燃料的方法。本文描述的方法生产的商品化学品也提供了。此外，还提供了商品化学品富集的、精炼生产的石油产品，以及生产这些产品的方法。