3,7,11-trimethyl-6,10-dodecadienal | 32480-08-3

• 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: 3,7,11-trimethyl-6,10-dodecadienal
• 英文别名: 2(3)-dihydrofarnesal；3,7,11-Trimethyl-dodeca-6,10-dienal；2,3-Dihydrofarnesal；3,7,11-trimethyldodeca-6,10-dienal
• CAS: 32480-08-3
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: ITBYWGRSPHMAEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3,7,11-trimethyl-6,10-dodecadienal 在 Amberlyst A-21 ion exchange resin 、 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 25.17h， 生成 5,9,13-trimethyl-2-nitro-2,8,12-tetradecatriene
  参考文献：
  名称：

  Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds

  摘要：

  Upon farnesylation by protein farnesyltransferase (FTase), key proteins become compartmentalized in cells. For example, cell membrane localization is essential for the mitogenic role of mutant Ras protein, which acts as a switch for cancer cell proliferation. We repel? that alpha -dicarbonyl compounds derived from the isoprenoid skeleton or other hydrophobic groups potently obstruct farnesylation of a Ras model peptide by human recombinant FTase in vitro. A geranyl-derived isoprenoid diketone, 5.9-dimethyl-8-decene-2,3-dione, at 17 muM caused a 62% reduction in FTase activity after 30 minutes. A farnesyl-derived isoprenoid diketone, 5,9,13-trimethyl-8,12-tetradecadiene-2,3-dione, at 93 muM caused a 94% reduction after 30 minutes. Other dicarbonyl:compounds found to be effective against FTase in vitro were (+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid, 4,4 ' -biphenyldiglyoxaldehyde, dehydroascorbic acid 6-palmitace, 2-oxododecanal, and phenylglyoxal. Higher concentrations of the alpha -dicarbonyl compound resulted in more rapid and more extensive inactivation. These findings demonstrate that ct-dicarbonyl compounds targeted to FTase interfere with protein farnesylation in vitro and may,lead to derivatives that have utility as chemotherapeutic agents.

  DOI：

  10.1002/1521-4184(200106)334:6<194::aid-ardp194>3.0.co;2-m
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 pyridinium chlorochromate 、 氢化铝 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 3,7,11-trimethyl-6,10-dodecadienal
  参考文献：
  名称：

  Inactivation of Protein Farnesyltransferase by Active-Site-Targeted Dicarbonyl Compounds

  摘要：

  Upon farnesylation by protein farnesyltransferase (FTase), key proteins become compartmentalized in cells. For example, cell membrane localization is essential for the mitogenic role of mutant Ras protein, which acts as a switch for cancer cell proliferation. We repel? that alpha -dicarbonyl compounds derived from the isoprenoid skeleton or other hydrophobic groups potently obstruct farnesylation of a Ras model peptide by human recombinant FTase in vitro. A geranyl-derived isoprenoid diketone, 5.9-dimethyl-8-decene-2,3-dione, at 17 muM caused a 62% reduction in FTase activity after 30 minutes. A farnesyl-derived isoprenoid diketone, 5,9,13-trimethyl-8,12-tetradecadiene-2,3-dione, at 93 muM caused a 94% reduction after 30 minutes. Other dicarbonyl:compounds found to be effective against FTase in vitro were (+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid, 4,4 ' -biphenyldiglyoxaldehyde, dehydroascorbic acid 6-palmitace, 2-oxododecanal, and phenylglyoxal. Higher concentrations of the alpha -dicarbonyl compound resulted in more rapid and more extensive inactivation. These findings demonstrate that ct-dicarbonyl compounds targeted to FTase interfere with protein farnesylation in vitro and may,lead to derivatives that have utility as chemotherapeutic agents.

  DOI：

  10.1002/1521-4184(200106)334:6<194::aid-ardp194>3.0.co;2-m

文献信息

• [EN] COMPOUNDS CAPABLE OF RELEASING FRAGRANT COMPOUNDS<br/>[FR] COMPOSÉS CAPABLES DE LIBÉRER DES COMPOSÉS ODORIFÉRANTS
  申请人：GIVAUDAN SA

  公开号：WO2012085287A1

  公开（公告）日：2012-06-28

  Provided is class of compounds of formula (I) wherein X, R1, R2 and R3 have the same meaning as given in the specification capable of releasing fragrant compounds in a controlled manner into the surroundings.

  提供的是具有化学式（I）的化合物类，其中X、R1、R2和R3的含义与规范中给出的相同，能够以受控方式释放香气化合物到周围环境中。
• Method for Producing Aldehyde and Ketone
  申请人：Yamashita Miyoshi

  公开号：US20110282102A1

  公开（公告）日：2011-11-17

  Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.

  提供了一种高效的生产醛和酮的方法，该方法廉价、具有高反应性，并能够在反应后轻松分离副产物。更具体地，提供了一种生产醛或酮的方法，包括至少一个氧化步骤，即在聚合物碳二亚胺（表示为以下式（1）且具有分子量为300至5000的重均分子量）和亚砜化合物的存在下氧化一级醇或二级醇，以及酸和碱，或者酸和碱的盐。
• 6-methoxy-2,6-dimethyloctanal and its use as a fragrance ingredient
  申请人：Givaudan S.A.

  公开号：EP1764355A1

  公开（公告）日：2007-03-21

  6-Methoxy-2,6-dimethyloctanal, a method of its production and fragrance compositions comprising it.

  6-甲氧基-2,6-二甲基辛醛，其生产方法和含有它的香精组合物。
• METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20150218072A1

  公开（公告）日：2015-08-06

  A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:

  揭示了一种生产式（1）的光学活性2,3-二氢法尼醛的方法。该方法包括在胺的锂盐存在下，使β-法尼烯（式2）经胺化反应得到（2E）-法尼基丙烯胺（一般式3）；将（2E）-法尼基丙烯胺经不对称异构化反应得到光学活性法尼基亚胺（一般式4）；以及将光学活性法尼基亚胺经溶剂解离：
• ALUMINIUM COMPLEXES AND USE THEREOF AS A CATALYST IN INTRAMOLECULAR RING CLOSURE REACTIONS
  申请人：Itoh Hisanori

  公开号：US20110319638A1

  公开（公告）日：2011-12-29

  To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al 1 (L 1 ) 1 (L 2 ) m (Lh) n ] k .

  提供一种方法，用于增加具有闭环的化合物和不具有闭环的化合物的光学异构体的比例，当具有甲醛基团和双键的化合物的光学异构体混合物在同一分子中发生羰基-烯环闭合反应时。一种增加光学异构体比例的方法，其特征在于将具有甲醛基团和双键的化合物的光学异构体混合物在预定的铝络合物的存在下进行环闭合反应，所述铝络合物由通用公式表示：[Al1(L1)1(L2)m(Lh)n]k。